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163 Houses

16

Newly Remodeled Townhome

Vermont / Jamaica

Jamaica townhouse

3 12 3 nights min

  • 3 bedrooms
  • sleeps 12
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$571

Price per night from

$571

(1) Excellent 

12

Charming and cozy Log cabin near Stratton Vermont

Vermont / Jamaica

Jamaica house

4 6 2 nights min

  • 4 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$342

Responds fast!
avg. 1 hour 24 minutes

Price per night from

$342

24

Live & Breathe VT- Village Home, Yoga Studio, Ski!

Vermont / Jamaica

Jamaica house

4 9 3 nights min

  • 4 bedrooms
  • sleeps 9
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$286

Price per night from

$286

24

Jamaica Townhome w/ Pool - Mins to Stratton Mtn!

Vermont / Jamaica

Jamaica house

2 12 min stay varies

  • 2 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$337

Responds fast!
avg. 22 minutes

Price per night from

$337

28

Stratton Ten Pines - Spectacular Timberframe Home

Vermont / Jamaica

Jamaica house

6 16 2 nights min

  • 6 bedrooms
  • sleeps 16
  • 2 nights min
  • Ski
  • Child Friendly
  • Pet Friendly

Price per night from

$1,718

Price per night from

$1,718

16

Classic Village Farmhouse with large yard & stream

Vermont / Jamaica

Jamaica house

4 9 7 nights min

  • 4 bedrooms
  • sleeps 9
  • 7 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$212

Price per night from

$212

7

Beautiful 5 BR/5 BA Home 10 mins from Stratton

Vermont / Jamaica

Jamaica house

5 11 2 nights min

  • 5 bedrooms
  • sleeps 11
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$1,028

Price per night from

$1,028

Great rentals within 20 miles that match your search

Distance approx 18.37 km from Jamaica

(1) Excellent 

4

Peaceful setting

Green Mountains / Dorset

Dorset house

3 5 3 nights min

  • 3 bedrooms
  • sleeps 5
  • 3 nights min
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$297

Price per night from

$297

Distance approx 16.8 km from Jamaica

24

Sunderland Vistas, STUNNING VIEWS, Sunset decks

Green Mountains / Manchester

Manchester house

5 10 2 nights min

  • 5 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$451

Price per night from

$451

Distance approx 16.42 km from Jamaica

17

Beautiful Cabin in a Peaceful 4 Season Resort with Club House Amenities

Vermont / Wilmington

Wilmington chalet

6 15 2 nights min

  • 6 bedrooms
  • sleeps 15
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$366

Price per night from

$366

Distance approx 13.94 km from Jamaica

(14) Excellent 

11

The Barn at Four Tooth Farm

Green Mountains / Manchester

Manchester house

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden
“Felt like home” First class in every way. Beautiful view from the "wall of windows". We found ourselves drinking coffee by the fireplace admiring the view late into the morning rather than getting up and at it.Top notch kitchen if your are inclined t
…see more

Price per night from

$300

Responds fast!
avg. 1 hour 49 minutes

Price per night from

$300

Distance approx 10.17 km from Jamaica

8

Blue Door Farm Cottage - SKI! Bromley 4mi., Magic 5mI., Stratton 12mi, Okemo..

Green Mountains / Peru

Peru house

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$191

Responds fast!
avg. 56 minutes

Price per night from

$191

Distance approx 12.92 km from Jamaica

9

Private Mountain Getaway

Vermont / Dover

Dover house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$137

Responds fast!
avg. 3 hours 47 minutes

Price per night from

$137

Distance approx 9.81 km from Jamaica

20

Casual lux near Hermitage Club & Four Columns Inn

Vermont / South Newfane

South Newfane villa

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 10 mi
  • Ski
  • Ask about children

Price per night from

$1,720

Price per night from

$1,720

Distance approx 11.18 km from Jamaica

22

Slopeside Townhome in Bromley Village

Green Mountains / Peru

Peru townhouse

4 11 2 nights min

  • 4 bedrooms
  • sleeps 11
  • 2 nights min
  • Child Friendly

Price per night from

$314

Price per night from

$314

Distance approx 13.62 km from Jamaica

(2) Excellent 

20

Five Bedroom Secluded Ski House Located Two Miles From Downtown Manchester

Green Mountains / Manchester

Manchester house

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$314

Price per night from

$314

Distance approx 6.11 km from Jamaica Show on Map

(6) Excellent 

18

Beautiful Vacation Home at Strattonwald at Stratton Mountain

Vermont / Stratton Mountain

Stratton Mountain house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Private garden

Price per night from

$514

Responds fast!
avg. 3 hours 35 minutes

Price per night from

$514

Distance approx 14.63 km from Jamaica

(1) Very Good 

10

Hugging Bear Inn - Tower Room

Vermont / Chester

Chester b and b

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 19 mi
  • Child Friendly
  • Air conditioning

Price per night from

$136

Price per night from

$136

Distance approx 17.56 km from Jamaica

21

New Lakefront Cedar Log Home

Vermont / Wilmington

Wilmington chalet

3 12 2 nights min

  • 3 bedrooms
  • sleeps 12
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary

Price per night from

$514

Responds fast!
avg. 1 hour 43 minutes

Price per night from

$514

Distance approx 5.99 km from Jamaica Show on Map

(2) Excellent 

12

2 Bedroom/2 Bath Condo

Vermont / Stratton Mountain

Stratton Mountain apartment

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly

Price per night from

$344

Price per night from

$344

Distance approx 13.53 km from Jamaica

(1) Very Good 

13

Beautiful Mountainside 2 Bedroom 2 Bath Condominium

Vermont / Dover

Dover condo

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 11 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$187

Price per night from

$187

Distance approx 14.63 km from Jamaica

11

Hugging Bear Inn - Bear's Den Room

Vermont / Chester

Chester b and b

1 5 1 night min

  • 1 bedroom
  • sleeps 5
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$159

Price per night from

$159

Distance approx 9.47 km from Jamaica

16

2016-17 Booking now for entire Ski Season $8000.00

Vermont / Londonderry

Londonderry chalet

3 7 3 nights min

  • 3 bedrooms
  • sleeps 7
  • 3 nights min
  • Child Friendly
  • Car not necessary

Price per night from

$400

Price per night from

$400

Distance approx 15.82 km from Jamaica

(1) Very Good 

13

Mount Snow Area Home with 5 Bedrooms

Vermont / Wilmington

Wilmington house

5 12 2 nights min

  • 5 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Pet Friendly

Price per night from

$343

Price per night from

$343

Distance approx 11.05 km from Jamaica

24

Awesome! 6BR, Secluded Hot Tub, sleeps 12, WIFI!!

Vermont / Dover

Dover house

6 12 2 nights min

  • 6 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly

Price per night from

$486

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$486

Distance approx 18.37 km from Jamaica

(1) Excellent 

15

3 BDR Farmhouse on Tranquil 105 acre Organic Farm

New Hampshire / Walpole

Walpole house

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Nearest beach 8 mi
  • Child Friendly
  • Air conditioning

Price per night from

$302

Price per night from

$302

Distance approx 17.95 km from Jamaica

28

NEW! Chester House on Working Farm Near Okemo!

Vermont / Proctorsville

Proctorsville house

5 14 min stay varies

  • 5 bedrooms
  • sleeps 14
  • min stay varies
  • Ski
  • Child Friendly
  • Pet Friendly

Price per night from

$287

Responds fast!
avg. 22 minutes

Price per night from

$287

Distance approx 11.35 km from Jamaica

26

West Dover Home w/Hot Tub- Short Drive to Mt. Snow

Vermont / Dover

Dover house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly

Price per night from

$223

Responds fast!
avg. 22 minutes

Price per night from

$223

Distance approx 14.64 km from Jamaica

32

Private Home w/ Views - Near Manchester Golf & Ski

Green Mountains / Dorset

Dorset house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$543

Responds fast!
avg. 22 minutes

Price per night from

$543

Distance approx 12.74 km from Jamaica

24

Chester House Just 12 Mins to Magic Mtn Ski Area!

Vermont / Chester

Chester house

5 8 min stay varies

  • 5 bedrooms
  • sleeps 8
  • min stay varies
  • Ski
  • Child Friendly
  • Pet Friendly

Price per night from

$155

Responds fast!
avg. 21 minutes

Price per night from

$155

Distance approx 14.55 km from Jamaica

10

The 1843 Stone House - Chester, VT (3bdrm/ 2 ba)

Vermont / Chester

Chester house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly

Price per night from

$200

Price per night from

$200

Distance approx 4.65 km from Jamaica

18

Vermont home located in the mountains between Mt. Snow & Stratton Mt

Vermont / Wardsboro

Wardsboro log cabin

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Private garden

Price per night from

$343

Price per night from

$343

Distance approx 15.25 km from Jamaica

19

Beautiful Ski/Golf Chalet on Hermitage Club golf course

Vermont / Wilmington

Wilmington house

4 11 min stay varies

  • 4 bedrooms
  • sleeps 11
  • min stay varies
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$286

Price per night from

$286

Distance approx 11.01 km from Jamaica

29

NEW! Slopeside Bromley Mtn House w/ Pool Table!

Green Mountains / Peru

Peru house

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$429

Responds fast!
avg. 22 minutes

Price per night from

$429

Distance approx 18.74 km from Jamaica

(3) Excellent 

20

Vermont 1828 Reunion House, sleeps 20, 5 miles to Okemo

Vermont / Proctorsville

Proctorsville house

8 20 2 nights min

  • 8 bedrooms
  • sleeps 20
  • 2 nights min
  • Ski
  • Child Friendly
  • Private garden

Price per night from

$457

Price per night from

$457

Distance approx 5.88 km from Jamaica

16

3 BR/Bth Townhouse/Condo Grt loc. Stratton Mtn. VT

Vermont / Stratton Mountain

Stratton Mountain apartment

3 8 90 nights min

  • 3 bedrooms
  • sleeps 8
  • 90 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$266

Price per night from

$266

Distance approx 11.96 km from Jamaica

30

West Dover Home w/Game Room-Pool & Fire Pit Access

Vermont / Dover

Dover house

5 13 min stay varies

  • 5 bedrooms
  • sleeps 13
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$326

Responds fast!
avg. 22 minutes

Price per night from

$326

Distance approx 5.11 km from Jamaica Show on Map

(9) Very Good 

10

Stratton 4 Bedroom Home

Vermont / Stratton Mountain

Stratton Mountain house

4 11 2 nights min

  • 4 bedrooms
  • sleeps 11
  • 2 nights min
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$400

Responds fast!
avg. 2 hours 54 minutes

Price per night from

$400