50 Best Vermont Vacation rentals on Holiday Lettings - Apartments

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House rentals Killington
203 properties
Vacation rentals Stowe
162 properties
Apartments Ludlow
66 properties
Northeast Kingdom
63 properties
Apartments Warren
49 properties
Green Mountains
44 properties
Wilmington
39 properties
Dover
32 properties
Jeffersonville
23 properties
South Hero
15 properties
North Hero
15 properties
Plymouth
10 properties
House rentals Stratton Mountain
9 properties
Alburgh
8 properties
Chester
8 properties
Woodstock
8 properties
Apartments Northfield
8 properties
Jamaica
8 properties
Colchester
7 properties
Fayston
7 properties

Vermont

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1,034 Vacation rentals

10

Vacation apartment in Richmond

Vermont / Richmond

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
Our clean and cozy studio apartment, set on 80 acres of woodland and pasture with views of Mt Mansfield to the north, offers a quiet and picturesque VT country retreat only 25 min from the city of Burlington. We have cross country ski and snowshoe trails out our door, …see more

from $100 / night

$500 / week

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from $100 / night

22

Vacation home in Westfield

Northeast Kingdom / Westfield

3 10 2 nights min

  • 3 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
This home in the hills of Vermont is less than five miles from Jay Peak Resort! Ski, skate and snowshoe in the winter and golf, hike, swim, and play tennis during the summer months. Available for short-term rental (minimum 2 night stay) and for seasonal rental. The home …see more

from $329 / night

$2,303 / week

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from $329 / night

18

Dorset Vacation home rental

Green Mountains / Dorset

8 23 2 nights min

  • 8 bedrooms
  • Sleeps 23
  • 2 nights min
  • Nearest beach 0.5 mi
  • Child friendly
  • Pet friendly
Our fully furnished 8 bedroom 3.5 bath ski Clubhouse in East Dorset, VT is available for rent in April - November. The house was significantly renovated in 2016. We are just north of the Emerald Lake Park entrance (3-5 min walk) and 1.9 miles north of the VT Horse Show …see more

from $140 / night

$900 - $2,685 / week

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avg. 15 minutes

from $140 / night

51

Perkinsville Vacation b&b rental

Vermont / Perkinsville

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
A beautiful bed and breakfast Vermont getaway! with 3 comfortable bedrooms available. Our place is a 200 year old farmhouse which is located in a big farm scenic private area in Perkinsville, Vermont. We have a covered bridge at one end of our road. It's quiet dirt road …see more

from $249 / night

$1,743 / week

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avg. 1 hour 56 minutes

from $249 / night

24

Ski home to rent in Vermont

Vermont / Woodstock

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ski
  • Child friendly
  • Pet friendly
Discover the tranquil and charismatic village of South Woodstock at this quaint 4-bedroom, 2-bathroom vacation rental cottage! 'Lilac Cottage' boasts 2,800 square feet of living space with, a fully equipped kitchen, accommodations for 8, and all the comforts of home. Si …see more

from $301 / night

$2,107 / week

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avg. 17 minutes

from $301 / night

37

Vermont ski home to rent.

Vermont / Wilmington

6 20 Min stay varies

  • 6 bedrooms
  • Sleeps 20
  • Min stay varies
  • Ski
  • Child friendly
Run away to this blissful blue vacation rental home ideally situated in the pastoral paradise of Wilmington! With 6 bedrooms, 4.5 bathrooms, and sleeping arrangements for 20, this immaculate abode is the ideal spot for a family reunion or retreat with friends. Whether y …see more

from $140 / night

$980 - $4,200 / week

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avg. 27 minutes

from $140 / night

12

Vacation home in Vermont

Vermont / Jamaica

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Pet friendly
Wonderful 2-story log cabin with 3 bedrooms, 2 baths and hardwood floors throughout. The most prominent feature of the house is the large floor to ceiling fireplace that is perfect after a long day of skiing. Home has full internet access, with Direct TV and large fla …see more

from $180 / night

$1,200 / week

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from $180 / night

32

Manchester Vacation home rental

Green Mountains / Manchester

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
Escape to scenic New England with a stay in this adorable two-story clapboard home. Adorned with a private deck, a beautiful sun room, and a superb location just steps from the golf course, this dog-friendly Manchester vacation rental is a welcome retreat any time of th …see more

from $89 / night

$623 / week

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avg. 3 hours 40 minutes

from $89 / night

34

Home rental in Jay

Northeast Kingdom / Jay

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Retreat to this resort condo with your family, and it just might become your favorite ski destination! The cozy interior provides a welcome home base for all the adventures that await you at Jay Peak Resort. Not only can you ski and snowboard to your heart's content, yo …see more

from $131 / night

$917 / week

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avg. 3 hours 40 minutes

from $131 / night

31

Vacation home in Vermont

Vermont / Dover

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly
Nestled in the forest of West Dover, this secluded home is the ideal place to experience the natural beauty of Vermont and escape the hectic pace of daily life. Three bedrooms plus a loft offer plenty of space for everyone in this dog-friendly cabin, complete with acces …see more

from $99 / night

$693 / week

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avg. 3 hours 40 minutes

from $99 / night

24

Ski cottage to rent in Island Pond

Northeast Kingdom / Island Pond

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ski
  • Child friendly
  • Pet friendly
*Please inquire with Evolve for discount specials through 6/30/18* For an unbelievable getaway, make 'Piece of Heaven' your home-away-from home in Island Pond Vermont. This incredible 2-bedroom, 1-bathroom vacation rental cottage sleeps 6 and grants visitors unbeatabl …see more

from $135 / night

$945 / week

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avg. 22 minutes

from $135 / night

(1) Excellent 

29

Vacation home in Jay

Northeast Kingdom / Jay

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Whether you're coming to dive into the fresh powder, check out the tree-lined trails, or play some golf, this ski-in, ski-out Jay Peak condo is ideal spot to enjoy them all! Offering six guests (four might be more comfortable) the chance to enjoy the prime location that …see more

from $175 / night

$1,225 / week

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avg. 3 hours 38 minutes

from $175 / night

35

Vacation home in Stratton Mountain

Vermont / Stratton Mountain

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
This Stratton Mountain home gives you the best of both worlds: cozy comforts for relaxation and easy access to incredible activities and amazing amenities all year-round! This Long Trail House condo offers access to a shared outdoor heated pool, sauna, and hot tubs, as …see more

from $91 / night

$637 / week

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avg. 3 hours 35 minutes

from $91 / night

(2) Excellent 

12

Vermont Vacation apartment accommodation

Vermont / Stratton Mountain

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
Fully renovated condo within easy walk to Stratton Village, with restaurants, shops and the slopes. Many Festivals throughout summer and fall. Granite countertops, tiled baths, new carpet, paint and furniture and outside deck. Winter views of the slopes. Free shuttle. W …see more

from $200 / night

$700 - $1,750 / week

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from $200 / night

(1) Very Good 

28

Vacation home in Vermont

Vermont / Bridgewater

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
It means no worries, for the rest of your vacation. No service, no problem! That's what makes this home so special, the stress of work and everyday life seem to evaporate the second you arrive. Being surrounded by beautiful scenery, fresh clean air and the sounds of nat …see more

from $214 / night

$1,150 - $1,638 / week

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avg. 1 hour 16 minutes

from $214 / night

(1) Very Good 

24

Ski log cabin to rent in Vermont

Vermont / Londonderry

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ski
  • Child friendly
  • Pet friendly
Your summer adventures begin at ‘West River Lodge,’ a warm and cozy 3-bedroom, 1-bathroom vacation rental log cabin, with accommodations for 6 in the southern Vermont woods. With 3.5 acres of private woodlands and a great location minutes from many summer activities (Ve …see more

from $155 / night

$1,085 / week

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avg. 27 minutes

from $155 / night

(1) Excellent 

18

Vacation home in Vermont

Vermont / South Pomfret

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
A beautifully appointed, New England style, separate 2 bedroom/2 bath 2 story main house located in a great area of Central/Southern Vermont. 2 minutes to the village of Woodstock. Biking/Hiking heaven with trails leading from the property- as well as 1 mile to the ski …see more

from $225 / night

$1,575 / week

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from $225 / night

(7) Very Good 

20

Cottage rental in Swanton

Vermont / Swanton

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
This direct-lakefront home is located on the western shore of Maquam Bay, a section of Lake Champlain with an excellent reputation for long-established properties, large lots, calmer waters, and minimal green algae. One mile South is the Missisquoi National Wildlife Ref …see more

from $135 / night

$1,400 / week

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from $135 / night

28

Vermont ski home to rent.

Vermont / Alburgh

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ski
  • Child friendly
Situated on beautiful Lake Champlain is this magnificent Alburgh vacation rental house, a 4-bedroom, 3.5-bathroom residence that offers the perfect combination of tranquil seclusion and a beautiful location! From picturesque views and included use of a canoe and 2 kayak …see more

from $149 / night

$1,043 / week

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avg. 37 minutes

from $149 / night

25

Ski log cabin to rent in Williamstown

Vermont / Williamstown

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Ski
  • Child friendly
Immerse yourself in the natural beauty of Williamstown when you book this 2-bedroom, 2-bathroom vacation rental cabin that comfortably sleeps 7. Situated on 70+ acres of beautiful woodlands, with hiking trails throughout and minutes from Vermont's finest attractions, th …see more

from $145 / night

$1,015 / week

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avg. 22 minutes

from $145 / night

(16) Excellent 

36

Vacation apartment in Vermont

Vermont / Woodstock

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
Escape to one of the prettiest towns in America. Make your vacation a quiet visit in a quintessential, charming apartment close to it all. We offer a ideal vacation rental: a new (2009) one bedroom log home apartment in the woods within walking distance of the Woodstock …see more

from $90 / night

$650 - $1,365 / week

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from $90 / night

(8) Excellent 

20

Cottage rental in Vermont

Vermont / South Hero

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Rustic Charm on the Southern end of South Hero. Up to 4 cottages available. 3 cottages are 2 bedrooms plus a twin daybed and 1 cottage has 1 queen bed plus a double futon on the enclosed heated porch. Weekly rentals only in July and August. 2 night minimum othe …see more

from $180 / night

$895 / week

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from $180 / night

(12) Excellent 

11

Home rental in Manchester

Green Mountains / Manchester

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Air conditioning
  • Private garden
The Barn at Four Tooth Farm is a luxury two-person vacation rental, privately located within walking distance of historic Manchester, Vermont in the shadow of Mt. Equinox, yet only a few hours drive from Boston and New York. The post-and-beam barn is tastefully design …see more

from $350 / night

$2,100 - $2,450 / week

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avg. 3 hours 21 minutes

from $350 / night

(17) Excellent 

Certificate of Excellence

26

Rupert Vacation home rental

Green Mountains / Rupert

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Pet friendly
Beautiful and private Vermont getaway on 17 acres of woods and fields. Spring is in the air and blooms are on the fruit trees. You will be greeted by colorful flowers and the birds will herald the morning sunrise. There is a slate patio with a barbeque, outside table …see more

Certificate of Excellence

from $180 / night

$1,000 - $2,470 / week

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from $180 / night

(4) Excellent 

20

Vacation chalet in West Wardsboro

Vermont / West Wardsboro

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
Secluded 2 level chalet in Scandia Village off Stratton-Arlington Rd. about 7" to Mt. Snow and 20" to Stratton Mountain . ski area. West Wardsboro Market nearby, and within walking distance.... Dover Vt. about 7 miles south on Rt. 100. Wilmington, Vt. about 25" …see more

from $175 / night

$800 - $1,000 / week

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avg. 1 hour 56 minutes

from $175 / night

24

Bridgewater ski apartment to rent.

Vermont / Bridgewater

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Ski
  • Child friendly
** Please note that there is another vacation rental unit on the premises, and there may be other travelers present during your stay.** Visit the scenic mountains of Vermont and stay at this 3-bedroom, 2-bathroom vacation rental apartment in Bridgewater Corners. This …see more

from $155 / night

$1,085 / week

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avg. 14 minutes

from $155 / night

14

Vacation apartment with shared pool in Fayston

Vermont / Fayston

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
Two bedroom condo at base of Mt Ellen (Sugarbush North) with million dollar view, wood burning fireplace and 2 full baths. Come be our guest at our year round mountain getaway in the Mad River Valley. Quintessential Vermont with refreshing mountain breezes in summer ne …see more

from $199 / night

$1,000 / week

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from $199 / night

34

Vacation home in Ludlow

Vermont / Ludlow

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Ski season has never been better than when enjoyed from this cozy Ludlow cabin with a foosball and Ping-Pong table! Enjoy some winter fun with the family, and bring along a few friends if you'd like since there's room for eight guests. Located just a mile and a half we …see more

from $89 / night

$623 / week

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avg. 3 hours 35 minutes

from $89 / night

(1) Excellent 

35

South Hero Vacation home rental

Vermont / South Hero

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
This delightful lakefront home on the southernmost island of Lake Champlain has a private dock and stunning lake views for up to 12 (eight adults maximum, please) guests to feel right at home! Sitting in a remote location on a sparsely-populated island, you'll find pea …see more

from $215 / night

$1,505 / week

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avg. 3 hours 46 minutes

from $215 / night

12

Vacation cottage in Vermont

Vermont / Charlotte

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
Crooked Path is the perfect spot to relax and reconnect with friends and family. Now available for summer and fall rentals May through September of 2015. The cottage boasts amazing views of the Adirondacks, Split Rock and Lake Champlain. Three bedrooms accommodate up to …see more

from $300 / night

$1,900 / week

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from $300 / night

(2) Excellent 

22

Log cabin rental in Burlington

Vermont / Burlington

5 12 2 nights min

  • 5 bedrooms
  • Sleeps 12
  • 2 nights min
  • Child friendly
  • Pet friendly
This is the perfect vacation house for the family that wants to get away from the frantic city life to enjoy the quiet relaxing life country life of fresh air, jogging on a dirt road, walking in the woods in hiking boots or snow boots. This 6500 square foot 3 story cabi …see more

from $795 / night

$5,565 / week

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from $795 / night

13

Vacation home in Rochester

Vermont / Rochester

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Private garden
Beautiful rustic log home situated only 1/2 hour to either Killington or Sugarbush Ski Resorts and is nestled in the Green Mountain National Forest with VAST and hiking trails nearby. Centrally located to many popular areas of Vermont, yet secluded for a quiet, relaxing …see more

from $250 / night

$1,500 - $2,050 / week

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from $250 / night

14

Vacation villa in Jeffersonville

Vermont / Jeffersonville

2 8 2 nights min

  • 2 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
INQUIRE FOR SHORTER STAYS Wyndham Smugglers’ Notch Vermont offers your family a special place to unwind, have fun and reconnect. Smugglers’ is a self-contained mountain resort village where each neighborhood, from wooded seclusion to close proximity to the Village Cent …see more

from $349 / night

$2,443 / week

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avg. 1 hour 3 minutes

from $349 / night

10

Walden Vacation cottage rental

Northeast Kingdom / Walden

2 6 6 nights min

  • 2 bedrooms
  • Sleeps 6
  • 6 nights min
  • Beach/lakeside relaxation
  • Nearest beach 11 mi
  • Child friendly
Rustic and nestled atop a 2200 ft.elevation mountain in Walden, Vt., this lakefront summer cabin has all the back-to-nature elements: quiet, clean air & water, cool breezes whistling in the spruces; loons, ducks, birds all swimming or flying by. You might even spot a m …see more

from $150 / night

$975 / week

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from $150 / night

34

Vacation b&b in Perkinsville

Vermont / Perkinsville

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
Come and enjoy a beach view in VT! refreshing yourself in a lovely beach painting room. Our place is a 200 year old farmhouse which is located in a big farm scenic private area in Perkinsville, Vermont. We have a covered bridge at one end of our road. It's quiet dirt ro …see more

from $79 / night

$553 / week

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avg. 1 hour 56 minutes

from $79 / night

29

Vacation home in Woodstock

Vermont / Woodstock

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
A quintessential Vermont getaway, this three-bedroom, two-bathroom Woodstock vacation rental features an outdoor fireplace, access to great skiing, plenty of room for up to six guests, and picturesque views next to the Ottauquechee River - all within a secluded woodland …see more

from $150 / night

$1,050 / week

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avg. 3 hours 40 minutes

from $150 / night

21

Vacation apartment rental

Vermont / Fairlee

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 3 mi
  • Child friendly
  • Private garden
This lake suite is located 5 minutes from Lake fairlee and 10 minutes from Lake Morey! We are within walking distance of many hiking trails and are surrounded by woods to explore! The apt/suite is located inside our large home on the bottom floor and has its own private …see more

from $99 / night

$693 / week

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from $99 / night

(1) Excellent 

27

Home rental in Vermont

Vermont / Londonderry

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Tucked away in the woods near Londonderry, Sherwood Escape offers visitors peace, quiet, and the comforts of home for up to eight guests (four adults). The warm wood interior complements the home's secluded setting, so make yourself comfortable in this spacious cabin! …see more

from $89 / night

$623 / week

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avg. 3 hours 35 minutes

from $89 / night

10

Vermont Vacation villa rental

Vermont / Wilmington

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Pet friendly
Adventure Awaits - whether skiing, hiking, swimming, or just reading a book, our home is the perfect place to getaway. Nestled in the woods, natural light floods the main living area with cathedral ceilings, skylights, and a wall of windows that looks out into the trees …see more

from $210 / night

$1,260 - $2,184 / week

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avg. 3 hours 10 minutes

from $210 / night

(1) Excellent 

21

Log cabin rental in Vermont

Vermont / Mount Holly

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Ripley Hill Cabin, our largest cabin, is located on a hill overlooking the Farm Pond, one of two swimming spots. It has a wood stove and a field-stone fireplace to warm a chilly evening. The cabin has two private bedrooms. One has a full bed and the second has a full be …see more

from $90 / night

$604 / week

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from $90 / night