Title: Middlesex County Vacation Rentals from $93: Search Short-Term Rentals | Expedia.com

[Middlesex County Travel Guide](https://expedia.com/Middlesex-County.dx553248635975177226)[Hotels in Middlesex County](https://expedia.com/Middlesex-County-Hotels.d553248635975177226.Travel-Guide-Hotels)[Flights to Middlesex County](https://expedia.com/Cheap-Flights-To-Middlesex-County.d553248635975177226.Travel-Guide-Flights)[Car Rentals in Middlesex County](https://expedia.com/Car-Rentals-In-Middlesex-County.d553248635975177226.Car-Rental-Guide)[Middlesex County Vacation Packages](https://expedia.com/Middlesex-County.d553248635975177226.Destination-Travel-Guides)

![Better than Dunns River Falls. Rope swings, jump off the falls into amazing turquoise blue water. Far fewer people](https://images.trvl-media.com/place/553248635209673480/780a0162-974c-427e-b049-593f2e948510.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Mike Gauthier

![](https://images.trvl-media.com/place/553248635209673480/780a0162-974c-427e-b049-593f2e948510.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=553248635975177226&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=553248635975177226&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=553248635975177226&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=553248635975177226&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Middlesex County vacation rentals

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/20000000/19530000/19521000/19520929/070b33b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/20000000/19530000/19521000/19520929/9a98d4a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/20000000/19530000/19521000/19520929/0bccaf84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, white sand](https://images.trvl-media.com/lodging/20000000/19530000/19521000/19520929/92a42a1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pipers Cove - Runaway Bay

[](https://www.expedia.com/Montego-Bay-Hotels-Pipers-Cove-Runaway-Bay.h19520929.Hotel-Information)

Runaway Bay

8.2/10

Very Good

(46 reviews)

"Place was in good condition 💯"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jovan

$153 nightly

$173 total

Feb 24 - Feb 25

Total with taxes and fees

[](https://www.expedia.com/Montego-Bay-Hotels-Pipers-Cove-Runaway-Bay.h19520929.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/50000000/49030000/49028600/49028580/16b8fd6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Apartment | Private kitchen | Cookware/dishes/utensils](https://images.trvl-media.com/lodging/50000000/49030000/49028600/49028580/adfe51ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Apartment | Individually furnished, blackout drapes, soundproofing](https://images.trvl-media.com/lodging/50000000/49030000/49028600/49028580/babb097e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Apartment | Living area | Flat-screen TV, books](https://images.trvl-media.com/lodging/50000000/49030000/49028600/49028580/16006680.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Caldo Tours

[](https://www.expedia.com/Ewarton-Hotels-Caldo-Tours.h49028580.Hotel-Information)

Ewarton

10/10

Exceptional

(3 reviews)

"Very inviting and the owner's are wonderful people that keeps you comfortable and satisfied "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephen

$90 nightly

$100 total

Feb 15 - Feb 16

Total with taxes and fees

[](https://www.expedia.com/Ewarton-Hotels-Caldo-Tours.h49028580.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/122000000/121300000/121290700/121290640/15397253.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/122000000/121300000/121290700/121290640/f986eeaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![10 outdoor pools](https://images.trvl-media.com/lodging/122000000/121300000/121290700/121290640/f02cd54e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining room](https://images.trvl-media.com/lodging/122000000/121300000/121290700/121290640/40d1a0aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Coolshade Villas - Richmond Estate

[](https://www.expedia.com/St-Anns-Bay-Hotels-Coolshade-Villas-Richmond-Estate.h121290640.Hotel-Information)

St. Ann's Bay

$214 nightly

$248 total

Feb 15 - Feb 16

Total with taxes and fees

[](https://www.expedia.com/St-Anns-Bay-Hotels-Coolshade-Villas-Richmond-Estate.h121290640.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106080000/106074600/106074531/a95c9d31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, Kitchen, Courtyard View | Private kitchen](https://images.trvl-media.com/lodging/107000000/106080000/106074600/106074531/7925ab33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106080000/106074600/106074531/14c9fd01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, Kitchen, Courtyard View | 2 bedrooms, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/107000000/106080000/106074600/106074531/efdcc75d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Serenity Oasis Apartment 

[](https://www.expedia.com/Spanish-Town-Hotels-Serenity-Oasis-Apartment.h106074531.Hotel-Information)

Spanish Town

$115 nightly

$133 total

Mar 17 - Mar 18

Total with taxes and fees

[](https://www.expedia.com/Spanish-Town-Hotels-Serenity-Oasis-Apartment.h106074531.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/28000000/27050000/27040700/27040675/8e10e97b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/28000000/27050000/27040700/27040675/4eab540c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/28000000/27050000/27040700/27040675/1104b528.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Food and drink](https://images.trvl-media.com/lodging/28000000/27050000/27040700/27040675/a5c38b94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountain Top Villa

[](https://www.expedia.com/Mandeville-Hotels-Mountain-Top-Villa.h27040675.Hotel-Information)

Mandeville

8.4/10

Very Good

(25 reviews)

"We enjoyed our stay at the villa, we stayed there for our honey moon, they even helped us take some really nice pics after our wedding"

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Daniel

$84 nightly

$93 total

Feb 15 - Feb 16

Total with taxes and fees

[](https://www.expedia.com/Mandeville-Hotels-Mountain-Top-Villa.h27040675.Hotel-Information)

![Private beach nearby](https://images.trvl-media.com/lodging/45000000/44260000/44252800/44252747/e38d034f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/45000000/44260000/44252800/44252747/97474acf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/45000000/44260000/44252800/44252747/f5de3ae3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior detail](https://images.trvl-media.com/lodging/45000000/44260000/44252800/44252747/df6fd64d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gorgeous Hideout

[](https://www.expedia.com/Montego-Bay-Hotels-Gorgeous-Hideout.h44252747.Hotel-Information)

Runaway Bay

10/10

Exceptional

(1 review)

"Host was very on top on things great safe area "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kevin

$185 nightly

$205 total

Feb 18 - Feb 19

Total with taxes and fees

[](https://www.expedia.com/Montego-Bay-Hotels-Gorgeous-Hideout.h44252747.Hotel-Information)

![Luxury Villa, 3 Bedrooms, Ensuite, Garden View | Egyptian cotton sheets, premium bedding, in-room safe](https://images.trvl-media.com/lodging/24000000/23590000/23588000/23587948/f86023a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Villa, 2 Bedrooms, 2 Bathrooms, Courtyard View | Living area | 50-inch flat-screen TV with cable channels, TV, DVD player](https://images.trvl-media.com/lodging/24000000/23590000/23588000/23587948/6fe90b5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Villa, 2 Bedrooms, 2 Bathrooms, Courtyard View | Living area | 50-inch flat-screen TV with cable channels, TV, DVD player](https://images.trvl-media.com/lodging/24000000/23590000/23588000/23587948/cd9aff03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Villa, 3 Bedrooms, Ensuite, Garden View (New 3) | Egyptian cotton sheets, premium bedding, in-room safe](https://images.trvl-media.com/lodging/24000000/23590000/23588000/23587948/de0a15e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Casa Princess Ocho Rios Vacation Villa

[](https://www.expedia.com/Montego-Bay-Hotels-Casa-Princess-Ocho-Rios-Vacation-Villa.h23587948.Hotel-Information)

Ocho Rios

9.4/10

Exceptional

(71 reviews)

"Beautiful, safe community and spacious property. Softer pillows would make it excellent"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

TRUDY ANN

$282 nightly

$299 total

Feb 15 - Feb 16

Total with taxes and fees

[](https://www.expedia.com/Montego-Bay-Hotels-Casa-Princess-Ocho-Rios-Vacation-Villa.h23587948.Hotel-Information)

![Family House, 2 Bedrooms, Accessible, Garden View | 2 bedrooms, Egyptian cotton sheets, premium bedding, in-room safe](https://images.trvl-media.com/lodging/14000000/13090000/13081000/13080939/1c5629b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family House, 2 Bedrooms, Accessible, Garden View | 2 bedrooms, Egyptian cotton sheets, premium bedding, in-room safe](https://images.trvl-media.com/lodging/14000000/13090000/13081000/13080939/3f8bed9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Villa, 2 Bedrooms, Accessible, Garden View | 2 bedrooms, Egyptian cotton sheets, premium bedding, in-room safe](https://images.trvl-media.com/lodging/14000000/13090000/13081000/13080939/5d2e02f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch flat-screen TV with cable channels, TV, DVD player](https://images.trvl-media.com/lodging/14000000/13090000/13081000/13080939/0fb66e83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Casa Victoria Golf Retreat

[](https://www.expedia.com/Kingston-Hotels-Casa-Victoria-Golf-Retreat.h13080939.Hotel-Information)

Kingston

9.8/10

Exceptional

(72 reviews)

"Our stay was very comfortable and relaxing,we didn't stay in but it had all the nesscessary things that we were looking for. I would recommend it to anyone who are travelling with their family to stay there.lovely place,!!"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Desmond

[](https://www.expedia.com/Kingston-Hotels-Casa-Victoria-Golf-Retreat.h13080939.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/120000000/119940000/119930200/119930136/b5b2e2bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/120000000/119940000/119930200/119930136/2dc773a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Villa, Private Pool, Pool View | In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/120000000/119940000/119930200/119930136/216ffe72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119940000/119930200/119930136/ef965154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Opulenz DraxHall

[](https://www.expedia.com/St-Anns-Bay-Hotels-Opulenz-DraxHall.h119930136.Hotel-Information)

St. Ann's Bay

$5,390 nightly

$6,199 total

Feb 15 - Feb 16

Total with taxes and fees

[](https://www.expedia.com/St-Anns-Bay-Hotels-Opulenz-DraxHall.h119930136.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/25000000/24930000/24925100/24925079/fb06c775.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/25000000/24930000/24925100/24925079/c85c98d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hartland Breeze

[](https://www.expedia.com/Montego-Bay-Hotels-Hartland-Breeze.h24925079.Hotel-Information)

St. Ann's Bay

10/10

Exceptional

(2 reviews)

"Good location. Friendly Host. Spotlessly clean. Very Safe. Very Quiet. Very close to many local beaches. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveler

$125 nightly

$145 total

Feb 15 - Feb 16

Total with taxes and fees

[](https://www.expedia.com/Montego-Bay-Hotels-Hartland-Breeze.h24925079.Hotel-Information)

![Family House, Garden View | Private kitchen | Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109990000/109981200/109981158/138c4d2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family House, Garden View | Living area](https://images.trvl-media.com/lodging/110000000/109990000/109981200/109981158/cfe793d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family House, Garden View | Living area](https://images.trvl-media.com/lodging/110000000/109990000/109981200/109981158/caef3e00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family House, Garden View | 2 bedrooms, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/110000000/109990000/109981200/109981158/e0c57e06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Phoenix Park Villas Portmore

[](https://www.expedia.com/Portmore-Hotels-Phoenix-Park-Villas-Portmore.h109981158.Hotel-Information)

Portmore

10/10

Exceptional

(5 reviews)

"I will definitely recommend that you stay here is so peaceful security are strictly on point with everything and the comfort of the home is great will be staying back for sure ."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kimoya

$218 nightly

$252 total

Feb 15 - Feb 16

Total with taxes and fees

[](https://www.expedia.com/Portmore-Hotels-Phoenix-Park-Villas-Portmore.h109981158.Hotel-Information)

![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/118000000/117150000/117143300/117143275/8b18fc2c_edited_54af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/118000000/117150000/117143300/117143275/bc723e27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/118000000/117150000/117143300/117143275/w3000h1872x0y0-393da8ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | 1 bedroom](https://images.trvl-media.com/lodging/118000000/117150000/117143300/117143275/1dd4413b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Adorable 1BR Cottage Walk to the Beach Priory

[](https://www.expedia.com/St-Anns-Bay-Hotels-Adorable-1BR-Cottage-Walk-To-The-Beach-Priory.h117143275.Hotel-Information)

St. Ann's Bay

$134 nightly

$155 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/St-Anns-Bay-Hotels-Adorable-1BR-Cottage-Walk-To-The-Beach-Priory.h117143275.Hotel-Information)

![On the beach, white sand](https://images.trvl-media.com/lodging/19000000/18330000/18326900/18326812/120cc534.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/19000000/18330000/18326900/18326812/26ce2c68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/19000000/18330000/18326900/18326812/d40dbdaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/19000000/18330000/18326900/18326812/1862a148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SandCastles Deluxe Beach Resort

[](https://www.expedia.com/Montego-Bay-Hotels-SandCastles-Deluxe-Beach-Resort.h18326812.Hotel-Information)

Ocho Rios

7.2/10

Good

(113 reviews)

"The room was clean plus the location was perfect "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Shawnette

$123 nightly

$138 total

Mar 6 - Mar 7

Total with taxes and fees

[](https://www.expedia.com/Montego-Bay-Hotels-SandCastles-Deluxe-Beach-Resort.h18326812.Hotel-Information)

![10 outdoor pools](https://images.trvl-media.com/lodging/122000000/121290000/121286200/121286187/05bf179f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining room](https://images.trvl-media.com/lodging/122000000/121290000/121286200/121286187/aaae377b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/122000000/121290000/121286200/121286187/e49afd43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/122000000/121290000/121286200/121286187/ac3c5921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relaxing Stay - Richmond Estate - 15mins Ocho Rios

[](https://www.expedia.com/St-Anns-Bay-Hotels-Relaxing-Apartment-With-Ocean-View.h121286187.Hotel-Information)

St. Ann's Bay

8.0/10

Very Good

(1 review)

"La habitación no es mala esta todo muy descuidado y no funcionan varias cosas "

![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg)

Eucario

$214 nightly

$248 total

Feb 15 - Feb 16

Total with taxes and fees

[](https://www.expedia.com/St-Anns-Bay-Hotels-Relaxing-Apartment-With-Ocean-View.h121286187.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/28000000/27480000/27477600/27477574/4970eaf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/28000000/27480000/27477600/27477574/a30ad0f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/28000000/27480000/27477600/27477574/69d233d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/28000000/27480000/27477600/27477574/799072b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Cottage very comfortable, relaxing also secure, 5 minutes walk from beach

[](https://www.expedia.com/Ocho-Rios-Hotels-The-Cottage-Very-Comfortable.h27477574.Hotel-Information)

Ocho Rios

9.6/10

Exceptional

(63 reviews)

"Great little cottage and very relaxing. Cozy space and super comfortable. Especially appreciated the access to a private beach which was wonderful."

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Natalee K.

$88 nightly

$95 total

Feb 16 - Feb 17

Total with taxes and fees

[](https://www.expedia.com/Ocho-Rios-Hotels-The-Cottage-Very-Comfortable.h27477574.Hotel-Information)

![2 outdoor pools](https://images.trvl-media.com/lodging/20000000/19110000/19105500/19105425/d4bcfe9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 2 Bedrooms, Pool Access, Garden View | In-room dining](https://images.trvl-media.com/lodging/20000000/19110000/19105500/19105425/15ff1fcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Villa, 3 Bedrooms, Accessible, Hill View | Private kitchen | Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19110000/19105500/19105425/001d9e03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Villa, 3 Bedrooms, Accessible, Hill View | View from room](https://images.trvl-media.com/lodging/20000000/19110000/19105500/19105425/e1aaba74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Country Club Villa I

[](https://www.expedia.com/Kingston-Hotels-The-Country-Club-Villa-I.h19105425.Hotel-Information)

Kingston

9.0/10

Wonderful

(10 reviews)

"The management team was awesome, the AC didn’t work in the main room on the first night but Ms Vicki made sure that I didn’t go a second night without it."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveler

[](https://www.expedia.com/Kingston-Hotels-The-Country-Club-Villa-I.h19105425.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/120000000/119150000/119142600/119142519/a86014ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119150000/119142600/119142519/eb4e4aa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining room](https://images.trvl-media.com/lodging/120000000/119150000/119142600/119142519/3332b202.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/120000000/119150000/119142600/119142519/ce99eb32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3BR Villa in Drax Hall Country Club

[](https://www.expedia.com/St-Anns-Bay-Hotels-3BR-Villa-In-Drax-Hall-Country-Club.h119142519.Hotel-Information)

St. Ann's Bay

$287 nightly

$331 total

Feb 15 - Feb 16

Total with taxes and fees

[](https://www.expedia.com/St-Anns-Bay-Hotels-3BR-Villa-In-Drax-Hall-Country-Club.h119142519.Hotel-Information)

![House | Pool | Outdoor pool](https://images.trvl-media.com/lodging/104000000/103250000/103244000/103243979/57de78d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | Interior](https://images.trvl-media.com/lodging/104000000/103250000/103244000/103243979/218780d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | Exterior detail](https://images.trvl-media.com/lodging/104000000/103250000/103244000/103243979/w826h443x1y0-d8745778.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | Living area](https://images.trvl-media.com/lodging/104000000/103250000/103244000/103243979/cd6f05e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Harbour Oasis Retreat - Charming 2 Bedroom House

[](https://www.expedia.com/Old-Harbour-Hotels-Remarkable-2-Bed-House-In-Old-Harbour.h103243979.Hotel-Information)

Old Harbour

$149 nightly

$173 total

Feb 22 - Feb 23

Total with taxes and fees

[](https://www.expedia.com/Old-Harbour-Hotels-Remarkable-2-Bed-House-In-Old-Harbour.h103243979.Hotel-Information)

![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/17000000/16110000/16104900/16104814/fa43eecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gift shop](https://images.trvl-media.com/lodging/17000000/16110000/16104900/16104814/8d69238d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, white sand](https://images.trvl-media.com/lodging/17000000/16110000/16104900/16104814/984004af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/17000000/16110000/16104900/16104814/74e06242.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ocho Rios Villa at Coolshade

[](https://www.expedia.com/Montego-Bay-Hotels-Ocho-Rios-Villa-At-Coolshade.h16104814.Hotel-Information)

St. Ann's Bay

9.8/10

Exceptional

(9 reviews)

"The host was wonderful and quite responsive. I will definately stay again and highly recomend. "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Oko

$621 nightly

$669 total

Feb 15 - Feb 16

Total with taxes and fees

[](https://www.expedia.com/Montego-Bay-Hotels-Ocho-Rios-Villa-At-Coolshade.h16104814.Hotel-Information)

![Cottage, 1 Bedroom, Patio, Beachside | Living area](https://images.trvl-media.com/lodging/105000000/104530000/104520700/104520638/176b6c16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage, 1 Bedroom, Patio, Beachside | Private kitchen](https://images.trvl-media.com/lodging/105000000/104530000/104520700/104520638/e155ab70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage, 1 Bedroom, Patio, Beachside | Living area](https://images.trvl-media.com/lodging/105000000/104530000/104520700/104520638/716de8f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/105000000/104530000/104520700/104520638/143f12ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Adorable 1Bed Cottage Walk to the Beach

[](https://www.expedia.com/St-Anns-Bay-Hotels-Adorable-1Bed-Cottage-Walk-To-The-Beach.h104520638.Hotel-Information)

St. Ann's Bay

8.0/10

Very Good

(4 reviews)

"Property was fine It is walking distance form a public beach Residential community area"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tricia

$94 nightly

$110 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/St-Anns-Bay-Hotels-Adorable-1Bed-Cottage-Walk-To-The-Beach.h104520638.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Middlesex+County%2C+Jamaica&regionId=553248635975177226&latLong=18.128002%2C-77.205589&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=CABIN)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Middlesex+County%2C+Jamaica&regionId=553248635975177226&latLong=18.128002%2C-77.205589&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=VILLA)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Middlesex+County%2C+Jamaica&regionId=553248635975177226&latLong=18.128002%2C-77.205589&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=VACATION_HOME)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Middlesex+County%2C+Jamaica&regionId=553248635975177226&latLong=18.128002%2C-77.205589&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=CONDO)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Middlesex+County%2C+Jamaica&regionId=553248635975177226&latLong=18.128002%2C-77.205589&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=APARTMENT)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Middlesex+County%2C+Jamaica&regionId=553248635975177226&latLong=18.128002%2C-77.205589&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=APART_HOTEL)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Middlesex+County%2C+Jamaica&regionId=553248635975177226&latLong=18.128002%2C-77.205589&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=COTTAGE)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Middlesex+County%2C+Jamaica&regionId=553248635975177226&latLong=18.128002%2C-77.205589&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=CHALET)

Residences

[](https://www.expedia.com/Hotel-Search?destination=Middlesex+County%2C+Jamaica&regionId=553248635975177226&latLong=18.128002%2C-77.205589&adults=2&startDate=2026-05-15&d1=2026-05-15&endDate=2026-05-18&d2=2026-05-18&lodging=RESIDENCE)

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## Top Middlesex County Hotel Reviews

![Morgans cliff](https://images.trvl-media.com/lodging/28000000/27300000/27291600/27291593/477af351_y.jpg)

### Morgans cliff

10/10 Excellent

"Room was clean and tastefully decorated. Love the Molton Brown toiletries! Views of pool and ocean were breath takingly beautiful. Staff were warm and welcoming and super helpful. Will definitely return when we are in the area. We highly recommend staying at Morgan's Cliff."

[](https://expedia.com/Montego-Bay-Hotels-Morgans-Cliff.h27291593.Hotel-Information)

![Whispering Seas](https://images.trvl-media.com/lodging/10000000/9370000/9362800/9362711/247a6e51_y.jpg)

### Whispering Seas

10/10 Excellent

"Spectacular views "

[](https://expedia.com/Montego-Bay-Hotels-Whispering-Seas.h9362711.Hotel-Information)

![Franklyn D. Resort & Spa](https://images.trvl-media.com/lodging/1000000/700000/690700/690644/8762ebfb_y.jpg)

### Franklyn D. Resort & Spa

10/10 Excellent

"FDR is a resort where families come back year after year. The staff is amazing and makes you feel at home. The food is great (especially for an all inclusive). The drinks are good (not cheap bad tasting alcohol). The kids have fun as they become friends with the other kids at the resort. And for the parents, it’s great to feel like you’re on vacation and not just parenting on vacation. The Nannie’s are a huge help. The rooms are very spacious with the kids having their own separate sleeping space and bathroom. The resort has remarkably recovered from Hurricane Melissa with the storm not impacting our stay at all. It was our second year in a row here. We love it (and so do our kids)!"

[](https://expedia.com/Runaway-Bay-Hotels-Franklyn-D-Resort-Spa-All-Inclusive.h690644.Hotel-Information)

![Little Savoy Guest House](https://images.trvl-media.com/lodging/92000000/91330000/91328400/91328381/7d3ea3af_y.jpg)

### Little Savoy Guest House

10/10 Excellent

"Everything was great the staff extra great. The amenities was great for the price of the place and it is so beautiful peaceful and quiet. Very cozy and comfortable. It is a place where you can have wedding reception party with friends or just a quiet spot for you and your partner. I will be going back there soon I love this place and it's not too far for the beach within walking distance and if you don't feel like walking the taxi stand is right around the corner and you can get to the beach less than five mins. Food places all around and if you drink bars and night clubs are all around as well. This is a great spot don't wait Book Your Trip Now!"

[](https://expedia.com/Runaway-Bay-Hotels-Little-Savoy-Guest-House.h91328381.Hotel-Information)

![Couples Tower Isle All Inclusive](https://images.trvl-media.com/lodging/1000000/530000/522100/522057/17fe4790_y.jpg)

### Couples Tower Isle All Inclusive

10/10 Excellent

"The best vacation I’ve had in years. Couples staff takes care of everything from the welcome right at the bus, to the way they get to know the guests. The room was clean and the amenities were unparalleled. I would recommend Couples resort to anyone who would here. Truly a magical experience."

[](https://expedia.com/Montego-Bay-Hotels-Couples-Tower-Isle-All-Inclusive.h522057.Hotel-Information)

![The Cardiff Hotel & Spa](https://images.trvl-media.com/lodging/1000000/30000/26700/26635/9cd8e947_y.jpg)

### The Cardiff Hotel & Spa

10/10 Excellent

"Courteousnesses, helpfulness and kindness "

[](https://expedia.com/Montego-Bay-Hotels-The-Cardiff-Hotel-Spa.h26635.Hotel-Information)

![Golf View Hotel](https://images.trvl-media.com/lodging/5000000/4670000/4663600/4663541/7d679efd_y.jpg)

### Golf View Hotel

10/10 Excellent

"The room and service was great "

[](https://expedia.com/Mandeville-Hotels-Golf-View-Hotel.h4663541.Hotel-Information)

![GoldenEye](https://images.trvl-media.com/lodging/55000000/54010000/54004700/54004628/61744773_y.jpg)

### GoldenEye

10/10 Excellent

"Gorgeous hotel very friendly lovely staff great setting shame had to pay for breakfast would prefer if included … "

[](https://expedia.com/Montego-Bay-Hotels-GoldenEye.h54004628.Hotel-Information)

![Sea Shell Palms](https://images.trvl-media.com/lodging/58000000/57970000/57966500/57966414/78973eea_y.jpg)

### Sea Shell Palms

10/10 Excellent

"Excellent as always. Exceptional staff"

[](https://expedia.com/Montego-Bay-Hotels-SEA-SHELL-PALMS.h57966414.Hotel-Information)

## Find out more about Middlesex County

**Everything you need to know about Middlesex County vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middlesex County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlesex County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Middlesex County vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Middlesex County. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middlesex County in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $93 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Middlesex County rentals**

At Expedia, we put the best Middlesex County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middlesex County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlesex County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlesex County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

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- [Vacation Homes in Middlesex County ](https://expedia.com/Middlesex-County-Private-Vacation-Homes.d553248635975177226-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Middlesex County ](https://expedia.com/Middlesex-County-Apartments.d553248635975177226-aaApartments.Travel-Guide-Accommodation)
- [Villas in Middlesex County ](https://expedia.com/Middlesex-County-Villas.d553248635975177226-aaVillas.Travel-Guide-Accommodation)
- [Condo Rentals in Middlesex County ](https://expedia.com/Middlesex-County-Condos.d553248635975177226-aaCondos.Travel-Guide-Accommodation)
- [Aparthotels in Middlesex County ](https://expedia.com/Middlesex-County-Apart-Hotels.d553248635975177226-aaApartHotels.Travel-Guide-Accommodation)
- [B&B in Middlesex County ](https://expedia.com/Middlesex-County-Bed-And-Breakfast.d553248635975177226-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cottages in Middlesex County ](https://expedia.com/Middlesex-County-Cottages.d553248635975177226-aaCottages.Travel-Guide-Accommodation)
- [Guest Houses in Middlesex County ](https://expedia.com/Middlesex-County-Guest-Houses.d553248635975177226-aaGuestHouses.Travel-Guide-Accommodation)
- [Resorts in Middlesex County ](https://expedia.com/Middlesex-County-Resorts.d553248635975177226-aaResorts.Travel-Guide-Accommodation)
- [Residences in Middlesex County ](https://expedia.com/Middlesex-County-Residences.d553248635975177226-aaResidences.Travel-Guide-Accommodation)
- [Cabin Rentals in Middlesex County ](https://expedia.com/Middlesex-County-Cabins.d553248635975177226-aaCabins.Travel-Guide-Accommodation)
- [Inns in Middlesex County ](https://expedia.com/Middlesex-County-Inns.d553248635975177226-aaInns.Travel-Guide-Accommodation)
- [Lodges in Middlesex County ](https://expedia.com/Middlesex-County-Lodges.d553248635975177226-aaLodges.Travel-Guide-Accommodation)
- [Treehouses in Middlesex County ](https://expedia.com/Middlesex-County-Treehouses.d553248635975177226-aaTreehouses.Travel-Guide-Accommodation)
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- [All-inclusive Resorts in North Coast](https://expedia.com/North-Coast-Hotels-All-Inclusive-Hotel.0-0-d6235803-tAllinclusiveHotel.Travel-Guide-Filter-Hotels)
- [Family Hotels in North Coast](https://expedia.com/North-Coast-Hotels-Family-Hotel.0-0-d6235803-tFamilyHotel.Travel-Guide-Filter-Hotels)
- [Hotels in Ocho Rios](https://expedia.com/Ocho-Rios-Hotels.d553248635209673480.Travel-Guide-Hotels)
- [All-inclusive Resorts in Negril](https://expedia.com/Negril-Hotels-All-Inclusive-Hotel.0-0-d2543-tAllinclusiveHotel.Travel-Guide-Filter-Hotels)
- [All-inclusive Resorts in Ocho Rios](https://expedia.com/Ocho-Rios-Hotels-All-Inclusive-Hotel.0-0-d553248635209673480-tAllinclusiveHotel.Travel-Guide-Filter-Hotels)
- [All-inclusive Resorts in Montego Bay](https://expedia.com/Montego-Bay-Hotels-All-Inclusive-Hotel.0-0-d180106-tAllinclusiveHotel.Travel-Guide-Filter-Hotels)
- [Adults Only Resorts & Hotels in Montego Bay](https://expedia.com/Montego-Bay-Hotels-Adults-Only-Resorts.0-0-d180106-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
- [All-inclusive Resorts in Kingston](https://expedia.com/Kingston-Hotels-All-Inclusive-Hotel.0-0-d180034-tAllinclusiveHotel.Travel-Guide-Filter-Hotels)
- [Palladium Hotels in Cornwall County](https://expedia.com/Cornwall-County-Hotels-Palladium.0-0-d553248635975177276--bPalladium.Travel-Guide-Filter-Hotels)
- [Hotels in Kingston](https://expedia.com/Kingston-Hotels.d180034.Travel-Guide-Hotels)
- [Hotels in North Coast](https://expedia.com/North-Coast-Hotels.d6235803.Travel-Guide-Hotels)
- [Hotels in Negril](https://expedia.com/Negril-Hotels.d2543.Travel-Guide-Hotels)
- [Adults Only Resorts & Hotels in Negril](https://expedia.com/Negril-Hotels-Adults-Only-Resorts.0-0-d2543-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)

Flights

- [Flights to Kingston](https://expedia.com/Cheap-Flights-To-Kingston.d180034.Travel-Guide-Flights)
- [Flights to Surrey County](https://expedia.com/Cheap-Flights-To-Surrey-County.d553248635975177212.Travel-Guide-Flights)
- [Flights to Montego Bay](https://expedia.com/Cheap-Flights-To-Montego-Bay.d180106.Travel-Guide-Flights)
- [Flights to Ocho Rios](https://expedia.com/Cheap-Flights-To-Ocho-Rios.d553248635209673480.Travel-Guide-Flights)

Cars

- [Car rentals in Montego Bay](https://expedia.com/Car-Rentals-In-Montego-Bay.d180106.Car-Rental-Guide)
- [Car rentals in Kingston](https://expedia.com/Car-Rentals-In-Kingston.d180034.Car-Rental-Guide)

Activities

- [Things to do in Ocho Rios](https://expedia.com/Things-To-Do-In-Ocho-Rios.d553248635209673480.Travel-Guide-Activities)
- [Things to do in Kingston](https://expedia.com/Things-To-Do-In-Kingston.d180034.Travel-Guide-Activities)
- [Things to do in Montego Bay](https://expedia.com/Things-To-Do-In-Montego-Bay.d180106.Travel-Guide-Activities)
- [Things to do in Mandeville](https://expedia.com/Things-To-Do-In-Mandeville.d8845.Travel-Guide-Activities)

Packages

- [Montego Bay All Inclusive Vacation Packages](https://expedia.com/lp/theme-vacations/all-inclusive-vacations/180106/Montego-Bay)
- [Montego Bay Vacation](https://expedia.com/Montego-Bay.d180106.Destination-Travel-Guides)
- [Ocho Rios Vacation](https://expedia.com/Ocho-Rios.d553248635209673480.Destination-Travel-Guides)

General

- [Visit Surrey County](https://expedia.com/Surrey-County.dx553248635975177212)
- [Visit Montego Bay](https://expedia.com/Montego-Bay.dx180106)
- [Visit North Coast](https://expedia.com/North-Coast.dx6235803)

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