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

Middlesex County Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Middlesex County vacation rentals

A beach with clear water, a sandy shore, and buildings in the background.

1. Fisherman's Point Resort

Fisherman's Point Resort
3.0 star property
Ocho Rios
6.0 out of 10, (621 reviews)
"Perfect location 👌"
United States
Shawnette
$79 nightly
The price is $91
Oct 15 - Oct 16
Total with taxes and fees
Fisherman's Point Resort
A resort with a large pool, lush greenery, and a view of the ocean.

2. Sky Castles

Sky Castles
2.5 star property
Ocho Rios
5.4 out of 10, (33 reviews)
"Was an ok experience "
United States
Rose
$133 nightly
The price is $147
Nov 6 - Nov 7
Total with taxes and fees
Sky Castles
A living room with a sofa, a coffee table, and a TV mounted on the wall. There is a kitchen area in the background with a window and a bar stool.

3. Wave Crest Resort Race Course

Wave Crest Resort Race Course
2.5 star property
Oracabessa
$106 nightly
The price is $123
Oct 8 - Oct 9
Total with taxes and fees
Wave Crest Resort Race Course
A balcony with a view of a pool and a building in the background.

4. 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
Oct 8 - Oct 9
Total with taxes and fees
Caldo Tours
A modern kitchen with a built-in oven, a refrigerator, and a dining area with a table set for four.

5. 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
$341 nightly
The price is $393
Oct 8 - Oct 9
Total with taxes and fees
Phoenix Park Villas Portmore
A pool area with a gazebo, lounge chairs, and a view of the surrounding landscape.

6. Mountain Top Villa

Mountain Top Villa
3.5 star property
Mandeville
8.4 out of 10, Very good, (27 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
Oct 8 - Oct 9
Total with taxes and fees
Mountain Top Villa
A person overlooking a coastal area with a cruise ship, lush greenery, and a swimming pool.

7. Spring Palm Estate

Spring Palm Estate
3.0 star property
Tower Isle
6.2 out of 10, (11 reviews)
"I would stay here again"
Canada
Shagufta
$77 nightly
The price is $83
Oct 8 - Oct 9
Total with taxes and fees
Spring Palm Estate
A resort with multiple swimming pools, lounge chairs, and umbrellas.

8. North Star Villa

North Star Villa
3.5 star property
Mammee Bay Estates
7.0 out of 10, Good, (7 reviews)
"We enjoyed our time at North Star Villa. The place was well kept, and Miss Norma was great."
United States
PATRICIA
$108 nightly
The price is $120
Oct 11 - Oct 12
Total with taxes and fees
North Star Villa
A large swimming pool with a clear view of the ocean in the background, surrounded by resort-style buildings.

9. 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
$389 nightly
The price is $448
Oct 8 - Oct 9
Total with taxes and fees
The Crest - Serenity Oasis Villa
A gated entrance with a central building and two smaller structures on either side.

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
$118 nightly
The price is $129
Oct 13 - Oct 14
Total with taxes and fees
DeJee Lodging
A resort with a large swimming pool, covered areas, and palm trees.

11. Villa at Richmond Estate

Villa at Richmond Estate
4.5 star property
St. Ann's Bay
5.0 out of 10, (2 reviews)
"This was an absolutely terrible experience, never in my entire life I have been treated like this after spending my money I highly recommend that this person be barred from using this platform for their shady business I was insulted by security guards telling me they are doing me a favor to sort out this woman’s incompetence we weren’t even given a code to enter the house we had to go back to security. The house was musty the sofa was grimy and smelly , not even a bottle of water was in the...
United States
Devon
$223 nightly
The price is $257
Oct 9 - Oct 10
Total with taxes and fees
Villa at Richmond Estate
A spacious living area with a high ceiling, a ceiling fan, a sofa set, a dining table with chairs, and a TV mounted on the wall.

12. DraxHall Villa

DraxHall Villa
2.0 star property
Saint Ann's Bay
2.0 out of 10, (1 review)
"I was not able to experience this property. The were no house address to go to or number to dial to connect with the host of this property. The was NO experience to review, or SHARE. This must be a PRANK or BAD dream"
United States
Brian
$291 nightly
The price is $336
Oct 8 - Oct 9
Total with taxes and fees
DraxHall Villa
A lush, green outdoor area with dense foliage and a variety of trees, including palm trees.

13. Xpress Vacations Lifestyle

Xpress Vacations Lifestyle
4.0 star property
Ocho Rios
$123 nightly
The price is $142
Oct 9 - Oct 10
Total with taxes and fees
Xpress Vacations Lifestyle
A bedroom with a bed, dresser, mirror, and curtains.

14. 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
$286 nightly
The price is $330
Oct 8 - Oct 9
Total with taxes and fees
3 Bedroom Cozy House in Drax Hall
A swimming pool with clear blue water, surrounded by a white fence and palm trees.

15. 1 Bed Villa - Sleeps 2 - Garden - Parking - Wifi

1 Bed Villa - Sleeps 2 - Garden - Parking - Wifi
3.5 star property
Ocho Rios
7.4 out of 10, Good, (3 reviews)
"I like Skycastles and Columbus Heights and stayed many times in this past. Its views are exceptional. This particular place was cheap. It had a futon for a sofa and plastic chairs for dinning and old seating outside. There were loads of locked spaces and it seamed cramped."
United States
Kristin
$93 nightly
The price is $107
Oct 9 - Oct 10
Total with taxes and fees
1 Bed Villa - Sleeps 2 - Garden - Parking - Wifi
A bed with a yellow and red bedspread in a room with white walls and a tiled floor.

16. Coke's Guest House

Coke's Guest House
2.0 star property
Mandeville
$86 nightly
The price is $99
Oct 8 - Oct 9
Total with taxes and fees
Coke's Guest House
Room

17. Cozy 1bed Apartment in Priory Walk to the Beach

Cozy 1bed Apartment in Priory Walk to the Beach
2.0 star property
St. Ann's Bay
$97 nightly
The price is $113
Oct 8 - Oct 9
Total with taxes and fees
Cozy 1bed Apartment in Priory Walk to the Beach
A living room with a sofa, a coffee table, a TV, and a bookshelf.

18. 1BR Comfort 15 mins Ocho Rios

1BR Comfort 15 mins Ocho Rios
2.0 star property
Richmond Estate
$208 nightly
The price is $241
Oct 8 - Oct 9
Total with taxes and fees
1BR Comfort 15 mins Ocho Rios
A modern living room with a white sofa, a glass coffee table, and a staircase leading to an upper level.

19. Tuscany Sun Villa at Legacy Townhouse

Tuscany Sun Villa at Legacy Townhouse
2.0 star property
Thompson Town
$750 nightly
The price is $864
Oct 8 - Oct 9
Total with taxes and fees
Tuscany Sun Villa at Legacy Townhouse
A two-story house with a yellow exterior and brown roof.

20. Ocho Rios at Coolshade Richmond

Ocho Rios at Coolshade Richmond
3.5 star property
St. Ann's Bay
2.0 out of 10, (1 review)
"Lack of communication was terrible Reached at the property, was double booked for multiples family. The host was not answering her phone and was difficult to reach due to lack of wifi access No hot upon reaching, was not mention to guest about turning on hot water system No change of linen No access to masterbed room bathroom for bathing due to broken pipe/facet in bath tub Leakage of water from toilet broken Only was thing,that was excited was the mango tree."
United States
Michelle f
$249 nightly
The price is $287
Oct 8 - Oct 9
Total with taxes and fees
Ocho Rios at Coolshade Richmond
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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Top Middlesex County Hotel Reviews

Couples Tower Isle All Inclusive

Couples Tower Isle All Inclusive

8/10 Good
"Na"
Atiah 5-night trip
Posted 9 hours ago
Couples Tower Isle 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 $83 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.