Vacation Rentals in Jamaica, VT

PRICE PER NIGHT

ACCOMMODATION TYPES

Spacious Riverfront Home 7 Minutes to Stratton!
9.8

Excellent

·
Jamaica
·
5 br
·
Sleeps 16
·
Waterfront · Hot Tub · Fireplace ·
From
$361/night
Check availability
Property
House · 5 Beds · 5 baths
Amenities
Waterfront
Hot Tub
Fireplace
In Unit Laundry
Furnished
Wifi
Onsite Management
Other spaces
Kitchen
Taylor Farm House + Guest House! - 6 bedroom / 5.5 bathroom
10

Excellent

·
Jamaica
·
6 br
·
Sleeps 20
·
Dishwasher · Oven · Fireplace ·
From
$387/night
Check availability
Property
House · 6 Beds · 6 baths
Amenities
Dishwasher
Oven
Fireplace
In Unit Laundry
Furnished
Wifi
Garage Parking
Onsite Management
Other spaces
Kitchen
This house is a 4 bedroom(s), 2.5 bathrooms, located in Jamaica, VT.
9.2

Excellent

·
Jamaica
·
4 br
·
Sleeps 10
·
Workspace · Hot Tub · Dishwasher ·
From
$336/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Hot Tub
Dishwasher
Oven
Fireplace
In Unit Laundry
Furnished
Wifi
Other spaces
Workspace, Kitchen
Stratton Mountain Home w/ View - 2 Mi to Ski Lift!
10

Excellent

·
Jamaica
·
2 br
·
Sleeps 6
·
Cable · Central Heat · Tv ·
From
$170/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Cable
Central Heat
Tv
Microwave
Ceiling Fan
Free Parking
Mountains
Oven
Other spaces
Kitchen
Authentic and comfortable Vermont log cabin - secluded yet near attractions
8.7

Very good

·
Jamaica
·
4 br
·
Sleeps 8
·
Air Conditioning · Dishwasher · Oven ·
From
$198/night
Check availability
Property
Apartment · 4 Beds · 2 baths
Amenities
Air Conditioning
Dishwasher
Oven
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
LOVELY Condo on Stratton Mountain
9.9

Excellent

·
Jamaica
·
2 br
·
Sleeps 4
·
Pool · Fireplace · Furnished ·
From
$256/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Pool
Fireplace
Furnished
Wifi
Swimming Pool
Fitness Center
Green Mountain Modern House: iconic modern getaway

No reviews

·
Jamaica
·
3 br
·
Sleeps 6
·
Workspace · Balcony · Air Conditioning ·
From
$438/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
Air Conditioning
Dishwasher
Oven
Fireplace
In Unit Laundry
Furnished
Wifi
Other spaces
Workspace, Balcony, Kitchen
The Woodland A-Frame: a midcentury Vermont getaway

No reviews

·
Jamaica
·
2 br
·
Sleeps 4
·
Balcony · Air Conditioning · Oven ·
From
$298/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Air Conditioning
Oven
Fireplace
In Unit Laundry
Furnished
Wifi
Other spaces
Balcony, Kitchen

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Birchside Cabin in the Woods
10

Excellent

·
Jamaica
·
4 br
·
Sleeps 8
·
Ski In Ski Out · On Site Laundry · Air Conditioning ·
From
$283/night
Check availability
Property
Apartment · 4 Beds · 2 baths
Amenities
Ski In Ski Out
On Site Laundry
Air Conditioning
Dishwasher
Oven
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
The Blue Spruce

No reviews

·
Jamaica
·
5 br
·
Sleeps 13
·
Ski In Ski Out · On Site Laundry · Dishwasher ·
From
$370/night
Check availability
Property
Apartment · 5 Beds · 3 baths
Amenities
Ski In Ski Out
On Site Laundry
Dishwasher
Oven
Fireplace
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
Jamaica Escape about 2 Mi to Stratton Mountain!

No reviews

·
Jamaica
·
4 br
·
Sleeps 9
·
Free Parking · Dishwasher · Oven ·
From
$619/night
Check availability
Property
Apartment · 4 Beds · 4 baths
Amenities
Free Parking
Dishwasher
Oven
Fireplace
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
Two Bedroom Chalet, Charming, Quiet, River Front
9.4

Excellent

·
Jamaica
·
2 br
·
Ski In Ski Out · On Site Laundry · Fitness Center ·
From
$199/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Ski In Ski Out
On Site Laundry
Fitness Center
Dishwasher
Oven
Fireplace
In Unit Laundry
Furnished
Other spaces
Kitchen
Newly renovated Stratton Vermont Ski House
10

Excellent

·
Jamaica
·
3 br
·
Sleeps 10
·
On Site Laundry · Pool · Fireplace ·
From
$716/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
On Site Laundry
Pool
Fireplace
In Unit Laundry
Furnished
Wifi
Swimming Pool
Other spaces
Kitchen
NEW! Jamaica Escape ~ 2 Mi to Stratton Mountain!
10

Excellent

·
Jamaica
·
4 br
·
Sleeps 9
·
Toiletries · Central Heat · Tv ·
From
$240/night
Check availability
Property
House · 4 Beds · 4 baths
Amenities
Toiletries
Central Heat
Tv
Microwave
Ceiling Fan
Free Parking
Dishwasher
Oven
Other spaces
Kitchen
Private Apt - 5 min drive to Stratton Mnt & 3 min WALK to Pikes Falls!!!
9.7

Excellent

·
Jamaica
·
1 br
·
Sleeps 5
·
Workspace · Outdoor Space · Mountains ·
From
$137/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Mountains
Oven
In Unit Laundry
Furnished
Wifi
Storage
Other spaces
Workspace, Kitchen
European Farmhouse on private 43 Acre Pond - Five minutes from Stratton Skiing
10

Excellent

·
Jamaica
·
5 br
·
Sleeps 10
·
Lake · Waterfront · Balcony ·
From
$916/night
Check availability
Property
House · 5 Beds · 5 baths
Amenities
Lake
Waterfront
Dishwasher
Oven
Fireplace
In Unit Laundry
Furnished
Wifi
Other spaces
Balcony, Kitchen
Forest Lodge - Near 6 Ski Resorts
6

Good

·
Jamaica
·
7 br
·
Sleeps 16
·
Hot Tub · Balcony · Air Conditioning ·
From
$1,236/night
Check availability
Property
House · 7 Beds · 5 baths
Amenities
Hot Tub
Air Conditioning
Mountains
Dishwasher
Oven
Fireplace
In Unit Laundry
Furnished
Other spaces
Balcony, Kitchen
Ski Stratton Mountain - walk/shuttle to slopes!’
9.9

Excellent

·
Jamaica
·
2 br
·
Sleeps 8
·
Ski In Ski Out · Fitness Center · Balcony ·
From
$260/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Ski In Ski Out
Fitness Center
Dishwasher
Oven
Fireplace
In Unit Laundry
Furnished
Wifi
Other spaces
Balcony, Kitchen
STRATTON SKI HOUSE BUILT FOR FUN, HOT TUB, SAUNA, MAN CAVE, MORE
10

Excellent

·
Jamaica
·
4 br
·
Smoking Allowed · Waterfront · Workspace ·
From
$891/night
Check availability
Property
House · 4 Beds · 4 baths
Amenities
Smoking Allowed
Waterfront
Hot Tub
Air Conditioning
Mountains
Dishwasher
Oven
Fireplace
Other spaces
Workspace, Balcony, Kitchen
Ski Chalet on private 35 acre property with hot tub + stratton vip parking pass
9.7

Excellent

·
Jamaica
·
4 br
·
Sleeps 12
·
Hot Tub · Dishwasher · Oven ·
From
$1,143/night
Check availability
Property
House · 4 Beds · 4 baths
Amenities
Hot Tub
Dishwasher
Oven
Fireplace
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
Stratton Mtn Resort Condo - NEW renovations! Seasonal avail
8

Very good

·
Jamaica
·
2 br
·
Sleeps 7
·
Hardwood Floor · Fitness Center · Pool ·
From
$200/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Hardwood Floor
Fitness Center
Pool
Mountains
Dishwasher
Oven
Fireplace
In Unit Laundry
Other spaces
Balcony, Kitchen
Foxglove Tiny House - a modern tiny getaway

No reviews

·
Jamaica
·
1 br
·
Sleeps 2
·
Assigned Parking · Balcony · Air Conditioning ·
From
$182/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Assigned Parking
Air Conditioning
Oven
Fireplace
In Unit Laundry
Furnished
Wifi
Other spaces
Balcony, Kitchen
Green Mountain Tiny House: a mountainside retreat

No reviews

·
Jamaica
·
1 br
·
Sleeps 2
·
Balcony · Air Conditioning · Oven ·
From
$200/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Air Conditioning
Oven
Fireplace
In Unit Laundry
Furnished
Wifi
Other spaces
Balcony, Kitchen
The Pine Mountain Hideaway minutes to Stratton! 4BR / 2 Bth
10

Excellent

·
Jamaica
·
4 br
·
Sleeps 16
·
Workspace · Outdoor Space · Fireplace ·
From
$306/night
Check availability
Property
House · 4 Beds · 2 baths
Amenities
Fireplace
In Unit Laundry
Furnished
Wifi
Garage Parking
Onsite Management
Other spaces
Workspace, Kitchen
Incredible Luxury 5BR Home with views of Stratton Mountain. No seasonal rental.
10

Excellent

·
Jamaica
·
5 br
·
Sleeps 14
·
Workspace · Hot Tub · Balcony ·
From
$714/night
Check availability
Property
House · 5 Beds · 5 baths
Amenities
Hot Tub
Mountains
Dishwasher
Oven
Fireplace
In Unit Laundry
Furnished
Wifi
Other spaces
Workspace, Balcony, Kitchen
Western Mountain Lodge on River and Close to Stratton
9.8

Excellent

·
Jamaica
·
5 br
·
Sleeps 14
·
Waterfront · Fitness Center · Dishwasher ·
From
$1,350/night
Check availability
Property
House · 5 Beds · 7 baths
Amenities
Waterfront
Fitness Center
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Wheelchair Accessible
Other spaces
Kitchen
Wishing Well Cabin
10

Excellent

·
Jamaica
·
3 br
·
Sleeps 8
·
Waterfront · Ski In Ski Out · Workspace ·
From
$336/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
Waterfront
Ski In Ski Out
Air Conditioning
Mountains
Dishwasher
Oven
In Unit Laundry
Furnished
Other spaces
Workspace, Kitchen
West Wing at Mantana Meadows on the West River
10

Excellent

·
Jamaica
·
2 br
·
Sleeps 8
·
Ev Charging · Waterfront · Workspace ·
From
$204/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Ev Charging
Waterfront
Air Conditioning
Mountains
Dishwasher
Oven
Fireplace
In Unit Laundry
Other spaces
Workspace, Kitchen
Stratton South Long Trail Studio Adjacent to the Village and Lifts
9.4

Excellent

·
Jamaica
·
Studio
·
Sleeps 4
·
On Site Laundry · Pool · Hot Tub ·
From
$208/night
Check availability
Property
Apartment · Studio · 1 bath
Amenities
On Site Laundry
Pool
Hot Tub
Air Conditioning
Mountains
Dishwasher
Oven
Fireplace
Other spaces
Balcony, Kitchen
Stratton Mtn view with hot tub!
10

Excellent

·
Jamaica
·
5 br
·
Sleeps 12
·
Ski In Ski Out · Workspace · Fitness Center ·
From
$983/night
Check availability
Property
House · 5 Beds · 3 baths
Amenities
Ski In Ski Out
Fitness Center
Hot Tub
Air Conditioning
Mountains
Dishwasher
Oven
Fireplace
Other spaces
Workspace, Kitchen
StylesBrook Townhouse - Great Location for Ski Families!
10

Excellent

·
Jamaica
·
4 br
·
Sleeps 8
·
On Site Laundry · Pool · Air Conditioning ·
From
$632/night
Check availability
Property
House · 4 Beds · 4 baths
Amenities
On Site Laundry
Pool
Air Conditioning
Mountains
Dishwasher
Oven
Fireplace
In Unit Laundry
Other spaces
Kitchen
Cozy Mountain Getaway
10

Excellent

·
Jamaica
·
4 br
·
Sleeps 8
·
Balcony · Dishwasher · Oven ·
From
$160/night
Check availability
Property
House · 4 Beds · 2 baths
Amenities
Dishwasher
Oven
In Unit Laundry
Furnished
Wifi
Other spaces
Balcony, Kitchen
Sweet Berry Farm
1

Poor

·
Jamaica
·
6 br
·
Sleeps 11
·
On Site Laundry · Dishwasher · Oven ·
From
$750/night
Check availability
Property
Apartment · 6 Beds · 5 baths
Amenities
On Site Laundry
Dishwasher
Oven
Fireplace
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
Enjoy Privacy and Beautiful views of Southern VT
9.8

Excellent

·
Jamaica
·
4 br
·
Sleeps 10
·
Fitness Center · Hot Tub · Outdoor Space ·
From
$283/night
Check availability
Property
House · 4 Beds · 4 baths
Amenities
Fitness Center
Hot Tub
Mountains
Dishwasher
Oven
Fireplace
In Unit Laundry
Furnished
Other spaces
Kitchen
5 Bedroom Condo at Stratton Mountain with Shuttle Service Slopes
10

Excellent

·
Jamaica
·
5 br
·
Sleeps 12
·
Carpet · Pool · Fireplace ·
From
$757/night
Check availability
Property
Condo · 5 Beds · 3 baths
Amenities
Carpet
Pool
Fireplace
In Unit Laundry
Furnished
Wifi
Swimming Pool
Fitness Center
Stratton Mountain Condo Close to Main Base & Village - Perfect Family Vacation!
10

Excellent

·
Jamaica
·
2 br
·
Ski In Ski Out · Fitness Center · Pool ·
From
$170/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Ski In Ski Out
Fitness Center
Pool
Hot Tub
Mountains
Dishwasher
Oven
Fireplace
Other spaces
Kitchen
3 Bedroom Stratton VT Luxury Walkable to Village
10

Excellent

·
Jamaica
·
3 br
·
Sleeps 8
·
Pool · Hot Tub · Fireplace ·
From
$590/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Pool
Hot Tub
Fireplace
Furnished
Wifi
Swimming Pool
Stratton Mountain Townhouse - Great Location For Ski Families!
9.8

Excellent

·
Jamaica
·
3 br
·
Sleeps 8
·
On Site Laundry · Pool · Outdoor Space ·
From
$650/night
Check availability
Property
Condo · 3 Beds · 3 baths
Amenities
On Site Laundry
Pool
Dishwasher
Oven
Fireplace
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
NEW! Family-Friendly Stratton Gem Close to Slopes!
10

Excellent

·
Jamaica
·
4 br
·
Sleeps 13
·
Toiletries · Assigned Parking · Walk In Closets ·
From
$450/night
Check availability
Property
Apartment · 4 Beds · 4 baths
Amenities
Toiletries
Assigned Parking
Walk In Closets
Cable
Lake
Central Heat
Tv
Microwave
Other spaces
Kitchen
Close to Stratton, Bromley & Magic! Four Season Location!
10

Excellent

·
Jamaica
·
3 br
·
Sleeps 10
·
Pool · Air Conditioning · Mountains ·
From
$300/night
Check availability
Property
Condo · 3 Beds · 2 baths
Amenities
Pool
Air Conditioning
Mountains
Dishwasher
Oven
Fireplace
In Unit Laundry
Furnished
Other spaces
Kitchen
Private Mountain Cottage With Hot Tub! Less than 2 Miles from Stratton Skiing!
8.9

Very good

·
Jamaica
·
2 br
·
Sleeps 4
·
Ski In Ski Out · Fitness Center · Pool ·
From
$219/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Ski In Ski Out
Fitness Center
Pool
Hot Tub
Mountains
Dishwasher
Oven
Fireplace
Other spaces
Kitchen
NEW! Jamaica Escape ~ 2 Mi to Stratton Mountain!
10

Excellent

·
Jamaica
·
4 br
·
Sleeps 9
·
Central Heat · Ceiling Fan · Air Conditioning ·
From
$335/night
Check availability
Property
House · 4 Beds · 4 baths
Amenities
Central Heat
Ceiling Fan
Air Conditioning
Dishwasher
Oven
Fireplace
In Unit Laundry
Furnished
Other spaces
Kitchen
Perfect family ski house with game room minutes to 4 mountains! Newly renovated!
10

Excellent

·
Jamaica
·
5 br
·
Sleeps 12
·
Lake · Waterfront · Mountains ·
From
$887/night
Check availability
Property
House · 5 Beds · 4 baths
Amenities
Lake
Waterfront
Mountains
Dishwasher
Oven
Fireplace
In Unit Laundry
Furnished
Other spaces
Kitchen
Entire Cabin - The Old Church - Mins from Stratton Mountain
9.4

Excellent

·
Jamaica
·
5 br
·
Sleeps 11
·
Ski In Ski Out · On Site Laundry · Fitness Center ·
From
$250/night
Check availability
Property
House · 5 Beds · 2 baths
Amenities
Ski In Ski Out
On Site Laundry
Fitness Center
Mountains
Dishwasher
Oven
In Unit Laundry
Furnished
Other spaces
Kitchen
Beautiful log cabin w/covered porch, fire pit, secluded - close to Stratton Mtn!
9.2

Excellent

·
Jamaica
·
4 br
·
Sleeps 11
·
Balcony · Dishwasher · Oven ·
From
$404/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Dishwasher
Oven
In Unit Laundry
Furnished
Garage Parking
Swimming Pool
Other spaces
Balcony, Kitchen
Tiny House with fire place. 5 min from Stratton Mt. 3 min WALK from Pikes Falls!
10

Excellent

·
Jamaica
·
Studio
·
Sleeps 2
·
Outdoor Space · Fireplace · In Unit Laundry ·
From
$178/night
Check availability
Property
House · Studio · 1 bath
Amenities
Fireplace
In Unit Laundry
Furnished
Wifi
Storage
Other spaces
Kitchen
Warm & Inviting Jamaica Cabin w/ Grill: Ski & Hike
10

Excellent

·
Jamaica
·
2 br
·
Sleeps 6
·
Garden · Tv · Microwave ·
From
$200/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Tv
Microwave
Ceiling Fan
Free Parking
Mountains
Oven
Fireplace
Wifi
Other spaces
Garden, Kitchen
Stratton Comfort & Convenience - Walk or Quick Shuttle to Village
10

Excellent

·
Jamaica
·
3 br
·
Sleeps 9
·
Fitness Center · Mountains · Dishwasher ·
From
$1,360/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Fitness Center
Mountains
Dishwasher
Fireplace
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
Rustic Cabin on Private Pond in Stratton Vermont
9.5

Excellent

·
Jamaica
·
2 br
·
Sleeps 4
·
Ceiling Fan · Waterfront · Air Conditioning ·
From
$176/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Ceiling Fan
Waterfront
Air Conditioning
Mountains
Dishwasher
Oven
Fireplace
In Unit Laundry
Other spaces
Kitchen
Comfortable House on a Private Pond in Stratton close to Stratton Ski Area.
9.6

Excellent

·
Jamaica
·
3 br
·
Sleeps 6
·
Walk In Closets · Waterfront · On Site Laundry ·
From
$215/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Walk In Closets
Waterfront
On Site Laundry
Air Conditioning
Dishwasher
Oven
Fireplace
In Unit Laundry
Other spaces
Kitchen
Showing 1 - 50 of 80 results
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Home > Vermont Vacation Rentals > Jamaica Vacation Rentals
Updated: March 28, 2023

Learn about vacation rentals in

Jamaica

Explore 80 vacation rentals near Jamaica, Vermont. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Jamaica, you can see photos of Jamaica vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Jamaica vacation rentals in specific areas. Whether you’re looking for a Jamaica staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Jamaica is $137 per night and the highest price is $1,360 per night.
14 of the vacation rentals near Jamaica are apartments or condos. The average bathroom count for this property type is 2. The median price for these vacation units is $256 per night. There are currently 7 vacation units under this price. 55 of the vacation rentals near Jamaica are houses. The average bathroom count for a vacation house near Jamaica is 3. The average price for vacation houses near Jamaica is $550 per night. There are 33 vacation homes under this price. The most common amenities for vacation rentals near Jamaica are: furnished, wifi, and kitchen. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.

1 bed rentals

4 available

2 bed rentals

16 available

3 bed rentals

14 available

4+ bed rentals

44 available

Which price range for vacation rentals is considered a good deal in Jamaica, VT area?

Vacation Rental Price Information in Jamaica, VT

The graph shows the percentages of vacation homes in each price bucket. Jamaica, VT has the largest percentage (37.70%) of homes in $500+ price range.
$0 - $50
6
units
$50 - $100
36
units
$100 - $150
36
units
$150 - $200
56
units
$200 - $250
61
units
$250 - $300
55
units
$300 - $350
35
units
$350 - $400
37
units
$400 - $450
25
units
$500+
210
units

Vacation Rentals in Jamaica, VT FAQ

How many vacation rentals in Jamaica are available?

There are currently 80 vacation rentals in Jamaica available. Our vacation rentals in Jamaica include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.

Are there any pet friendly vacation rentals in Jamaica?

Yes, right now there are 24 pet friendly vacation rentals in Jamaica. A pet friendly vacation rental in Jamaica means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.

Are there any vacation rentals in Jamaica with a pool?

Yes there are vacation rentals with a pool available in Jamaica, VT. View more detailed vacation spots on Vacations by Zumper.

Are there any vacation rentals in Jamaica with internet access?

As of March 28, 2023, there are vacation rentals with internet access available in Jamaica, Vermont. Check out more enjoyable destinations on Vacations by Zumper.

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