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Middlesex County Vacation Rentals

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Our top choices for Middlesex County vacation rentals

1. Fisherman's Point Resort

Fisherman's Point Resort
3.0 star property
Ocho Rios
6.0 out of 10, (629 reviews)
"Perfect location 👌"
United States
Shawnette
The price is CA $84
CA $128 total
includes taxes & fees
Dec 1 - Dec 2
Fisherman's Point Resort

2. Adorable 1Bed Cottage Walk to the Beach

Adorable 1Bed Cottage Walk to the Beach
2.0 star property
St. Ann's Bay
8.4 out of 10, Very good, (5 reviews)
"Love the convenience and it was very nice and comfortable. Will book again. Cute n friendly little dog on property as well"
United States
Marisa
The price is CA $65
CA $147 total
includes taxes & fees
Nov 9 - Nov 10
Adorable 1Bed Cottage Walk to the Beach

3. Wave Crest Resort Race Course

Wave Crest Resort Race Course
2.5 star property
Oracabessa
10.0 out of 10, Exceptional, (1 review)
"The host came out to greet us. Very warm welcome. Large rooms. Clean. Friendly and very helpful staff. Would definitely stay here again !!"
United States
Beverly
The price is CA $191
CA $221 total
includes taxes & fees
Nov 9 - Nov 10
Wave Crest Resort Race Course

4. 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, (72 reviews)
"We had access to the beach which was nice."
United States
Vanessa
The price is CA $102
CA $131 total
includes taxes & fees
Dec 6 - Dec 7
The Cottage very comfortable, relaxing also secure, 5 minutes walk from beach

5. 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, (63 reviews)
"This property was unique close to the beach very clean host was very good love this place"
United States
Rose
The price is CA $110
CA $126 total
includes taxes & fees
Nov 10 - Nov 11
Spacious contemporary, relaxing apartment only 5 minutes walk to fabulous beach

6. 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, (61 reviews)
"Excellent location..bottom floor entrance with parking only a few steps away."
Canada
Osmond
The price is CA $125
CA $179 total
includes taxes & fees
Nov 25 - Nov 26
Light escape mixes luxury with homey - 2 mins from the beach!

7. 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
The price is CA $95
CA $182 total
includes taxes & fees
Nov 18 - Nov 19
DeJee Lodging

8. 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
The price is CA $83
CA $132 total
includes taxes & fees
Nov 9 - Nov 10
Mountain Top Villa

9. Lovely 1-bed Cottage in St Catherine

Lovely 1-bed Cottage in St Catherine
3.0 star property
Ewarton
10.0 out of 10, Exceptional, (1 review)
"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
The price is CA $25
CA $41 total
includes taxes & fees
Nov 21 - Nov 22
Lovely 1-bed Cottage in St Catherine

10. 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
The price is CA $161
CA $179 total
includes taxes & fees
Nov 25 - Nov 26
North Star Villa

11. Luxe Beach Front Retreat

Luxe Beach Front Retreat
Ocho Rios
8.2 out of 10, Very good, (16 reviews)
"Very decent space, host is also super attentive."
United States
Jaimie
The price is CA $149
CA $201 total
includes taxes & fees
Nov 9 - Nov 10
Luxe Beach Front Retreat

12. Cosy & Stylish Studio at Turtle Beach Towers - Pool, Beach & Town Nearby

Cosy & Stylish Studio at Turtle Beach Towers - Pool, Beach & Town Nearby
Ocho Rios
8.4 out of 10, Very good, (83 reviews)
"It was a very nice stay. The location was everything. I will be back"
United States
darlisa w.
The price is CA $133
CA $163 total
includes taxes & fees
Nov 9 - Nov 10
Cosy & Stylish Studio at Turtle Beach Towers - Pool, Beach & Town Nearby

13. Sky Castles

Sky Castles
2.5 star property
Ocho Rios
5.4 out of 10, (33 reviews)
"Was an ok experience "
United States
Rose
The price is CA $124
CA $171 total
includes taxes & fees
Nov 10 - Nov 11
Sky Castles

14. Tamaras Inn

Tamaras Inn
Ocho Rios
7.0 out of 10, Good, (6 reviews)
"Ant infestation old filthy pillows non working stove and hungry feral cat are why the rate is so low. Not for the squeamish. Best part? The downstairs tenant and his son."
United States
William
The price is CA $64
CA $95 total
includes taxes & fees
Nov 9 - Nov 10
Tamaras Inn

15. 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, (26 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
The price is CA $110
CA $140 total
includes taxes & fees
Nov 9 - Nov 10
Spacious contemporary Studio Apartment with swimming pool 5 mins walk from beach

16. Adorable 1bed Cottage Too Walk to the Beach

Adorable 1bed Cottage Too Walk to the Beach
2.0 star property
St. Ann's Bay
The price is CA $77
CA $144 total
includes taxes & fees
Nov 9 - Nov 10
Adorable 1bed Cottage Too Walk to the Beach

17. Sandcastles Ocho Rios

Sandcastles Ocho Rios
5.0 star property
Ocho Rios
3.4 out of 10, (15 reviews)
"To have specific details on all properties "
Canada
Gregory
The price is CA $57
CA $155 total
includes taxes & fees
Dec 6 - Dec 7
Sandcastles Ocho Rios

18. 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
The price is CA $165
CA $183 total
includes taxes & fees
Nov 9 - Nov 10
Caldo Tours

19. Coke's Guest House

Coke's Guest House
2.0 star property
Mandeville
The price is CA $121
CA $140 total
includes taxes & fees
Nov 9 - Nov 10
Coke's Guest House

20. SOL Euphoria Ocho Rios walk to the beach

SOL Euphoria Ocho Rios walk to the beach
2.0 star property
Ocho Rios
The price is CA $171
CA $368 total
includes taxes & fees
Nov 9 - Nov 10
SOL Euphoria Ocho Rios walk to the beach
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

Find out more about Middlesex County

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middlesex County. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.