Middlesex County Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Tonight
Nov 18 - Nov 19
Tomorrow
Nov 19 - Nov 20
This weekend
Nov 21 - Nov 23
Next weekend
Nov 28 - Nov 30

Vacation Rentals in Middlesex County

Family House, Garden View | Living area
Phoenix Park Villas Portmore

Phoenix Park Villas Portmore

4.0 star property
Portmore
10.0 out of 10, Exceptional, (3)
"Very clean,quiet neighborhood and great customer service "
United States
SHAWN
$152 nightly
The price is $176
Nov 29 - Nov 30
Total with taxes and fees
Phoenix Park Villas Portmore
Outdoor pool
Mountain Top Villa

Mountain Top Villa

3.5 star property
Mandeville
8.4 out of 10, Very Good, (23)
"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
Daniel
$84 nightly
The price is $93
Nov 20 - Nov 21
Total with taxes and fees
Mountain Top Villa
Exterior
Opulenz DraxHall

Opulenz DraxHall

3.5 star property
St. Ann's Bay
$5,390 nightly
The price is $6,199
Nov 20 - Nov 21
Total with taxes and fees
Opulenz DraxHall
Outdoor pool, pool umbrellas, sun loungers
Caldo Tours

Caldo Tours

2.5 star property
Ewarton
10.0 out of 10, Exceptional, (3)
"Very inviting and the owner's are wonderful people that keeps you comfortable and satisfied "
United States
Stephen
$90 nightly
The price is $100
Nov 20 - Nov 21
Total with taxes and fees
Caldo Tours
Family House, 2 Bedrooms, Accessible, Garden View | 2 bedrooms, Egyptian cotton sheets, premium bedding, in-room safe
Casa Victoria Golf Retreat

Casa Victoria Golf Retreat

4.0 star property
Kingston
9.0 out of 10, Wonderful, (81)
"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
Desmond
$207 nightly
The price is $227
Nov 21 - Nov 22
Total with taxes and fees
Casa Victoria Golf Retreat
Apartment, Kitchen, Courtyard View | Terrace/patio
Serenity Oasis Apartment

Serenity Oasis Apartment

2.0 star property
Spanish Town
$115 nightly
The price is $133
Nov 20 - Nov 21
Total with taxes and fees
Serenity Oasis Apartment
2 outdoor pools
The Country Club Villa I

The Country Club Villa I

3.5 star property
Kingston
9.0 out of 10, Wonderful, (10)
"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
Anonymous traveler
$227 nightly
The price is $241
Nov 29 - Nov 30
Total with taxes and fees
The Country Club Villa I
Outdoor pool
The Cottage very comfortable, relaxing also secure, 5 minutes walk from beach

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

Ocho Rios
9.6 out of 10, Exceptional, (59)
"We rented this cottage back in January for 5 weeks. We're back for 2.5 weeks and are still loving it. Chris the property manager is great and always comes through, whatever you need. The beach is 5 minutes walk away and has a wonderful restaurant with great food and service. "
Canada
Diane P.
$85 nightly
The price is $91
Nov 20 - Nov 21
Total with taxes and fees
The Cottage very comfortable, relaxing also secure, 5 minutes walk from beach
TV
Charming refuge at Colbeck Manor

Charming refuge at Colbeck Manor

Old Harbour
10.0 out of 10, Exceptional, (2)
"Host Duwayne was excellent, very attentive, house was clean and comfy. Would stay again "
United States
chin
$174 nightly
The price is $179
Nov 20 - Nov 21
Total with taxes and fees
Charming refuge at Colbeck Manor
Private beach nearby
Gorgeous Hideout

Gorgeous Hideout

3.0 star property
Runaway Bay
10.0 out of 10, Exceptional, (1)
"Host was very on top on things great safe area "
United States
Kevin
Gorgeous Hideout
Cottage | Exterior
Lovely 1-bed Cottage in St Catherine Jamaica

Lovely 1-bed Cottage in St Catherine Jamaica

3.0 star property
Ewarton
10.0 out of 10, Exceptional, (1)
"I enjoyed my stay at the cottage, hosts were very helpful and my stay was very quiet and peaceful. Will definitely stay here again in the future."
United States
DESMOND
$30 nightly
The price is $35
Dec 1 - Dec 2
Total with taxes and fees
Lovely 1-bed Cottage in St Catherine Jamaica
Dining room
Cozy Relaxing Home in Old Harbour

Cozy Relaxing Home in Old Harbour

2.0 star property
Old Harbour
$34,887 nightly
The price is $40,121
Nov 29 - Nov 30
Total with taxes and fees
Cozy Relaxing Home in Old Harbour
Interior
Charming 2-bedroom house in Portmore with WiFi, AC

Charming 2-bedroom house in Portmore with WiFi, AC

Portmore
10.0 out of 10, Exceptional, (5)
"A well appointed and neatly organized dwelling nestled within Kingston port-side residential community for the traveler on the go for a day, a week or an extended stay. Best to book well in advance for accommodations."
United States
Kojo
$110 nightly
The price is $110
Nov 20 - Nov 21
Total with taxes and fees
Charming 2-bedroom house in Portmore with WiFi, AC
Exterior
Adorable 1Bed Cottage Walk to the Beach

Adorable 1Bed Cottage Walk to the Beach

2.0 star property
St. Ann's Bay
8.0 out of 10, Very Good, (4)
"Property was fine It is walking distance form a public beach Residential community area"
United States
Tricia
$94 nightly
The price is $110
Nov 20 - Nov 21
Total with taxes and fees
Adorable 1Bed Cottage Walk to the Beach
Family Studio Suite, Mountain View | Living area | Printers
Thebreeze2022

Thebreeze2022

2.5 star property
May Pen
$51 nightly
The price is $60
Nov 24 - Nov 25
Total with taxes and fees
Thebreeze2022
Property grounds
2Bedrooms 2Bathroom - Swimming pool - Gated community - Drier - Free Wifi

2Bedrooms 2Bathroom - Swimming pool - Gated community - Drier - Free Wifi

Ocho Rios
9.6 out of 10, Exceptional, (23)
"Quiet and relaxing stay. "
United States
Jennifer S.
$197 nightly
The price is $197
Nov 24 - Nov 25
Total with taxes and fees
2Bedrooms 2Bathroom - Swimming pool - Gated community - Drier - Free Wifi
On the beach, white sand
Pipers Cove - Runaway Bay

Pipers Cove - Runaway Bay

3.0 star property
Runaway Bay
8.4 out of 10, Very Good, (45)
"Place was in good condition 💯"
United States
Jovan
$153 nightly
The price is $173
Nov 25 - Nov 26
Total with taxes and fees
Pipers Cove - Runaway Bay
Terrace/patio
Carib Waves

Carib Waves

2.0 star property
Ocho Rios
$151 nightly
The price is $175
Nov 21 - Nov 22
Total with taxes and fees
Carib Waves
Apartment | 1 bedroom
Adorable 1BR Cottage Walk to the Beach Priory

Adorable 1BR Cottage Walk to the Beach Priory

2.0 star property
St. Ann's Bay
$137 nightly
The price is $158
Nov 20 - Nov 21
Total with taxes and fees
Adorable 1BR Cottage Walk to the Beach Priory
Terrace/patio
Drax Hall Country Club's Sweet Escape

Drax Hall Country Club's Sweet Escape

3.5 star property
Ocho Rios
8.0 out of 10, Very Good, (3)
"The AC is not working there is only two beds, not three beds that was stated by the host!!! She had another guest at the house at 11am on us which is very unprofessional I rate it a 5 out of 10 "
United States
Samuel
Drax Hall Country Club's Sweet Escape
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlesex County Hotel Reviews

Bahia Principe Grand Jamaica - All Inclusive

Bahia Principe Grand Jamaica - All Inclusive

10/10 Excellent
"Staff was awesome. The hotel itself was close to activities in ochi. Highly recommend "
Tori 5-night trip
Posted 5 days ago
Bahia Principe Grand Jamaica - All Inclusive

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 $60 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