Search Cottages in Jamaica

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
26 Sep - 28 Sep
In one month
10 Oct - 12 Oct
In two months
7 Nov - 9 Nov
In three months
5 Dec - 7 Dec

Cottages in Jamaica

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Exterior

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (230)
"Extremely cozy. Would highly recommend staying here."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Exterior

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

10.0 out of 10, Exceptional, (17)
"We very much enjoyed our stay in this historic, architecturally significant home. We would definitely stay here again."
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Exterior

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.6 out of 10, Excellent, (57)
"really enjoyed our stay. Place would be much better if there was a microwave."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Vermont Country Cottage (Near Village)
Exterior

Vermont Country Cottage (Near Village)

9.4 out of 10, Exceptional, (14)
"Cute place. Enjoyed our stay. "
Vermont Country Cottage (Near Village)
Rare new Home on Lake Whitingham. Semi-priv beach
Exterior

Rare new Home on Lake Whitingham. Semi-priv beach

10.0 out of 10, Exceptional, (5)
"This home is spectacular, built on a hillside overlooking a pond. Very tastefully built into the landscape. Inside was very well appointed and plenty of room for our family. Three bathrooms was a big plusCould have spent the entire day lookjng out the windows"
Rare new Home on Lake Whitingham. Semi-priv beach
Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!
Exterior

Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!

10.0 out of 10, Exceptional, (28)
"Loved Dorset and this house was great. Very clean and living area was nice to spend time with family. Also close to skiing which we took advantage of"
Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow
Exterior

Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow

9.6 out of 10, Exceptional, (66)
"We enjoyed our stay in this cozy cabin on the ridge. The owners have great taste and they have thought of everything to make the stay pleasant. "
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access
Exterior

Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

8.8 out of 10, Excellent, (3)
"Perfect cottage on the water!! Enjoyed kayaking and pedal boat with family. Beautiful greenery! Very quick respond."
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access
Home with a spring-fed pond and mountain view.
Exterior

Home with a spring-fed pond and mountain view.

10.0 out of 10, Exceptional, (119)
"This house was fantastic. We didn’t have the best weather this Memorial Day weekend but the house, pond and view made up for it. Jeremy stocked the house with everything we could possibly need including fresh eggs from the resident chickens, bacon, snacks and so much more. It was quiet and the bed was super comfortable. Our dog enjoyed watching the beautiful fish in the pond and visiting the chickens. We can’t wait to return!"
Home with a spring-fed pond and mountain view.
Lake life at Woodford Cottage
Exterior

Lake life at Woodford Cottage

9.6 out of 10, Exceptional, (15)
"Perfect getaway for a family ski trip."
Lake life at Woodford Cottage
Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!
House (3 Bedrooms) | Interior

Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great place "
Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!
Near Hiking & Skiing: Home in Wilmington!
House (3 Bedrooms) | Interior

Near Hiking & Skiing: Home in Wilmington!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Owner Brent was helpful and quick to respond to questions. The house is near Mount Snow great for skiing! Very nice place to stay, we will definitely stay again when booking for next year."
Near Hiking & Skiing: Home in Wilmington!
Near Skiing & Hiking: Quiet Home in West Wardsboro
House (4 Bedrooms) | Interior

Near Skiing & Hiking: Quiet Home in West Wardsboro

3.0 star property
Near Skiing & Hiking: Quiet Home in West Wardsboro
Rustic Marlboro Cottage: 4 Mi to Lake Raponda!
Cottage (2 Bedrooms) | Interior

Rustic Marlboro Cottage: 4 Mi to Lake Raponda!

3.0 star property
Rustic Marlboro Cottage: 4 Mi to Lake Raponda!
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
Exterior

This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.

10.0 out of 10, Exceptional, (28)
"This was a great location… close to town but also close to skiing, hiking and skating."
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
Cozy Wilmington Home: 6 Mi to Mount Snow!
House (4 Bedrooms) | Interior

Cozy Wilmington Home: 6 Mi to Mount Snow!

3.0 star property
Cozy Wilmington Home: 6 Mi to Mount Snow!
< 6 Mi to Arlington: 'whimsical Stone Abode!'
Cottage (1 Bedroom) | Interior

< 6 Mi to Arlington: 'whimsical Stone Abode!'

3.0 star property
10.0 out of 10, Exceptional, (1)
"We came into town for a few days to visit friends. This was a perfect place. The home was clean and very inviting! Quiet location. Fully stocked kitchen with all the appliances and cooking ware you may need. You will not regret staying here. We loved the photo album of how the home was built! "
< 6 Mi to Arlington: 'whimsical Stone Abode!'
Wilmington Vacation Rental Near Hiking and Skiing!
House (4 Bedrooms) | Interior

Wilmington Vacation Rental Near Hiking and Skiing!

3.0 star property
Wilmington Vacation Rental Near Hiking and Skiing!
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
TV, books

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

10.0 out of 10, Exceptional, (8)
"Great, clean, charming cottage. The hosts are amazing and communicated every detail, very hospitable. Highly recommend. "
The price is SAR 1,347
SAR 1,649 total
includes taxes & fees
25 Sep - 26 Sep
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
House (2 Bedrooms) | Interior

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

3.0 star property
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Jamaica Hotel Reviews

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Friendly staff . Very clean."
Nancy 1-night trip
Posted 3 days ago
Hampton Inn and Suites Manchester

Frequently asked questions

Why book your cottage in Jamaica with Expedia?
Reserving a cottage in Jamaica is as easy as working out your travel dates and picking your ideal place for a vacation in the outdoors. From upmarket retreats to inexpensive properties and cottages that feature perks like free WiFi, Expedia has something for all tastes. As for the best deals around? We've got you covered!
How can I find cheap cottages in Jamaica?
With Expedia's handy filter tool, comparing cheap cottages in Jamaica is a snap. To discover accommodations that'll make your hip pocket happy, narrow down your search by budget, amenities and star rating.