A waterfall cascading into a turquoise pool surrounded by lush greenery.

Middlesex County Vacation Rentals

  • 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

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Middlesex County vacation rentals

Exterior

1. Caldo Tours

Caldo Tours
2.5 star property
Ewarton
10.0 out of 10, Exceptional, (3 reviews)
"Very inviting and the owner's are wonderful people that keeps you comfortable and satisfied "
United States
Stephen
$117 nightly
The price is $130
Aug 16 - Aug 17
Total with taxes and fees
Caldo Tours
Cottage, 1 Bedroom, Patio, Beachside | Beach/ocean view

2. 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 reviews)
"A proper home from home just a wonderful place to stay "
United Kingdom
Peppa
$97 nightly
The price is $113
Aug 16 - Aug 17
Total with taxes and fees
Adorable 1Bed Cottage Walk to the Beach
Terrace/patio

3. Serenity Oasis Apartment

Serenity Oasis Apartment
2.0 star property
Spanish Town
$106 nightly
The price is $122
Aug 23 - Aug 24
Total with taxes and fees
Serenity Oasis Apartment
Outdoor pool

4. Mountain Top Villa

Mountain Top Villa
3.5 star property
Mandeville
8.2 out of 10, Very Good, (28 reviews)
"Hotal it self was beautiful , lay out great , room was a bit small but manageable. Overall a great stay I would highly recommend"
United Kingdom
Robert
$84 nightly
The price is $93
Aug 16 - Aug 17
Total with taxes and fees
Mountain Top Villa
Luxury Apartment | 2 bedrooms, Tempur-Pedic beds, blackout drapes, soundproofing

5. Xpress Vacations Lifestyle

Xpress Vacations Lifestyle
4.0 star property
Ocho Rios
$133 nightly
The price is $155
Sep 14 - Sep 15
Total with taxes and fees
Xpress Vacations Lifestyle
Outdoor pool

6. 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
9.4 out of 10, Exceptional, (69 reviews)
"The host was very friendly and the room was clean and came equipped with air conditioning."
Canada
Shereeka
$87 nightly
The price is $94
Aug 25 - Aug 26
Total with taxes and fees
The Cottage very comfortable, relaxing also secure, 5 minutes walk from beach
Outdoor pool

7. 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, (29 reviews)
"Overall a perfect stay for 2 people or couples "
United States
Devon
$211 nightly
The price is $211
Aug 17 - Aug 18
Total with taxes and fees
2Bedrooms 2Bathroom - Swimming pool - Gated community - Drier - Free Wifi
Interior

8. Charming refuge at Colbeck Manor

Charming refuge at Colbeck Manor
Old Harbour
10.0 out of 10, Exceptional, (2 reviews)
"Host Duwayne was excellent, very attentive, house was clean and comfy. Would stay again "
United States
chin
$162 nightly
The price is $166
Aug 16 - Aug 17
Total with taxes and fees
Charming refuge at Colbeck Manor
On the beach

9. Light escape mixes luxury with homey - 2 mins from the beach!

Light escape mixes luxury with homey - 2 mins from the beach!
Ocho Rios
9.6 out of 10, Exceptional, (58 reviews)
"Travel from Nashville Tennessee for a 5 day stay, from start to finish the communication was on point. Anything missed was address within a reasonable timeframe.. If you’re thinking about getting the place, just go ahead and get it. we definitely will be staying here again in the future. There’s not much to say other than come.. come and enjoy a secluded stay. Thank you Everton ✊ respect"
United States
Denise
$127 nightly
The price is $127
Aug 19 - Aug 20
Total with taxes and fees
Light escape mixes luxury with homey - 2 mins from the beach!
Front of property

10. DeJee Lodging

DeJee Lodging
3.5 star property
Ocho Rios
9.0 out of 10, Wonderful, (4 reviews)
"The facility is safe clean attractive and the rooms have everything you needed for ur comfort experience was wonderful 100/100👍"
United States
Winston
$116 nightly
The price is $127
Sep 2 - Sep 3
Total with taxes and fees
DeJee Lodging
Family House, Garden View | Private kitchen | Full-size fridge, microwave, oven, stovetop

11. Phoenix Park Villas Portmore

Phoenix Park Villas Portmore
4.0 star property
Portmore
9.8 out of 10, Exceptional, (6 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
Kimoya
$256 nightly
The price is $296
Aug 19 - Aug 20
Total with taxes and fees
Phoenix Park Villas Portmore
Apartment | 2 bedrooms, iron/ironing board, WiFi (free), bed sheets

12. Immaculate 2-bed Apartment in Spanish Town

Immaculate 2-bed Apartment in Spanish Town
3.0 star property
Spanish Town
$67 nightly
The price is $78
Aug 20 - Aug 21
Total with taxes and fees
Immaculate 2-bed Apartment in Spanish Town
Beach nearby, sun loungers

13. Spacious contemporary, relaxing apartment only 5 minutes walk to fabulous beach

Spacious contemporary, relaxing apartment only 5 minutes walk to fabulous beach
Mammee Bay Estates
8.8 out of 10, Excellent, (61 reviews)
"This property was unique close to the beach very clean host was very good love this place"
United States
Rose
$100 nightly
The price is $108
Aug 17 - Aug 18
Total with taxes and fees
Spacious contemporary, relaxing apartment only 5 minutes walk to fabulous beach
Exterior

14. Home in St. Catherine section 2

Home in St. Catherine section 2
Spanish Town
9.0 out of 10, Wonderful, (2 reviews)
"Have no complaints, my stay was a great stay "
United States
Icashea M.
$128 nightly
The price is $128
Aug 19 - Aug 20
Total with taxes and fees
Home in St. Catherine section 2
Children's activities

15. Villa at The Palms

Villa at The Palms
3.5 star property
St. Ann's Bay
8.0 out of 10, Very Good, (2 reviews)
"The villa was very family oriented . The pool area very clean and enjoyable. Surrounding very quiet and clean, location very nice."
United States
Michelle
$208 nightly
The price is $240
Aug 16 - Aug 17
Total with taxes and fees
Villa at The Palms
6 outdoor pools

16. The Crest - Serenity Oasis Villa

The Crest - Serenity Oasis Villa
2.0 star property
St. Ann's Bay
8.0 out of 10, Very Good, (1 review)
"Location is beautiful and very secure and safe. The house and pool were lovely as well. "
United States
Laura
$298 nightly
The price is $343
Sep 2 - Sep 3
Total with taxes and fees
The Crest - Serenity Oasis Villa
Property grounds

17. Spacious contemporary Studio Apartment with swimming pool 5 mins walk from beach

Spacious contemporary Studio Apartment with swimming pool 5 mins walk from beach
Mammee Bay Estates
9.0 out of 10, Wonderful, (25 reviews)
"Really enjoyed my stay, place was very clean, comfortable, quiet, it is close to the town and other attractions plus Mr Ludford, the property manager was very very kind, respectful and help...Will definitely return"
United States
DENISE
$100 nightly
The price is $108
Aug 17 - Aug 18
Total with taxes and fees
Spacious contemporary Studio Apartment with swimming pool 5 mins walk from beach
Full-size fridge, toaster, cookware/dishes/utensils

18. Royal Palm Luxury Villas

Royal Palm Luxury Villas
3.0 star property
Ocho Rios
$265 nightly
The price is $306
Aug 19 - Aug 20
Total with taxes and fees
Royal Palm Luxury Villas
Beach

19. Comfy bedrooms with swimming pool plus free wifi, spa hut, bbq, 24-hour security

Comfy bedrooms with swimming pool plus free wifi, spa hut, bbq, 24-hour security
Mammee Bay Estates
9.0 out of 10, Wonderful, (19 reviews)
"This is really 2 bedrooms and a hallway with access to a basic open kitchenette. Hot water and AC are good and access to beach around the corner is very convenient. Ok accommodations for a night or 2 but def not a "villa" experience. (Take your own towels). Greeter was helpful and pleasant"
United States
CLARE
$126 nightly
The price is $136
Aug 17 - Aug 18
Total with taxes and fees
Comfy bedrooms with swimming pool plus free wifi, spa hut, bbq, 24-hour security
Family House | WiFi (free)

20. 3 Bedroom Cozy House in Drax Hall

3 Bedroom Cozy House in Drax Hall
3.5 star property
Ocho Rios
4.0 out of 10, (1 review)
"Last minute while at airport I received an email to say that the place reserved was no longer available. After being on the phone for over an hour I was offered another place which was smaller. I had no choice but to take it or me and my kids would have been on the street. Upon entering the place, it was immediately noticed that it was not clean, no light bulbs, 1 tv in one of the bedrooms. Front door did not close properly. Cushions ripped up. I got the impression that the place was on the...
United States
Samantha
$229 nightly
The price is $264
Aug 17 - Aug 18
Total with taxes and fees
3 Bedroom Cozy House in Drax Hall
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 Escape Runaway Bay - Hyatt Inclusive Collection - Adults Only - All Inclusive

Bahia Principe Escape Runaway Bay - Hyatt Inclusive Collection - Adults Only - All Inclusive

8/10 Good
"The entertainment and restaurant staff was very friendly others wise the customer service need more work"
Giselle 2-night trip
Posted 13 hours ago
Bahia Principe Escape Runaway Bay - Hyatt Inclusive Collection - Adults Only - 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 $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.