Vacation rentals in Whitingham

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Top-rated vacation rentals in Whitingham

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Guest favorite

Apartment in Shelburne Falls

4.98 out of 5 average rating, 485 reviews

In town, newly renovated studio with private deck

Come explore our unique area and stay in a newly renovated, light filled studio with private entrance, secluded deck , kitchenette and bath located in the quaint New England village of Shelburne Falls.We are within easy walking distance to numerous shops, candlepin bowling, Glacial potholes, tennis/basketball courts, Bridge of Flowers, eateries/restaurants, Pothole pictures, groceries, playgrounds, hiking & swimming areas, a natural food store and art galleries.Close to Berkshire East and Zoar!

Mar 17 – 24

G$20,186 GYD per night

Guest favorite

Apartment in Wilmington

4.91 out of 5 average rating, 109 reviews

Globetrotter Retreat too - Minutes to the Mountain

Newly renovated, fully furnished in heart of quaint mountain village; minutes to Mount Snow, Green Mountains & lakes. Year round outdoor activities: snow sports in winter, watersports/hiking in summer. Quiet 1 bedroom apt on 2nd floor sleeps 4 people in comfort. Private balcony overlooks tranquil woods & rolling river. Steps to restaurants, bars & shopping. Supermarket is a short walk. Free Moover bus stop across the street ride for free to local destinations! 18 years or older guests only.

Apr 26 – May 3

G$21,149 GYD per night

Guest favorite

Home in Wilmington

4.99 out of 5 average rating, 171 reviews

Vermont Sugar House Retreat

Stay at this unique rustic Vermont getaway. Nestled on a quiet hill in Wilmington, this private retreat will serve as the perfect home base for your Vermont adventures. You'll have the house to yourself without a neighbor in sight. While very private and surrounded by beautiful forest, this house is still only a short 5 minute drive from downtown Wilmington. The house is built around an enormous one-of-a-kind natural stone fireplace that was formed atop the old foundations of a sugar house.

May 9 – 16

G$44,834 GYD per night

Guest favorite

Tiny home in Wilmington

4.99 out of 5 average rating, 136 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Sep 10 – 17

G$44,854 GYD per night

Guest favorite

Apartment in Wilmington

4.97 out of 5 average rating, 126 reviews

The Loft @ Adams Farm-a great stay near Mt. Snow

Spacious & clean in Historic Duplex Farmhouse located minutes from MT Snow Ski Area & Stratton for Skiing, Snowboarding & Tubing. VAST trails just across the road. Shop & eat in the quaint villages of Wilmington & Dover. Private entrance and 3-stories of space with farmstyle decor & lovely views. 0ver 100-acres for you to Snowshoe , X-Country ski or just hike & explore. Plenty of parking for snowmobile trailers. Walking distance to Local Farm Store. Our pool is available July 1-Labor Day

Apr 24 – May 1

G$25,700 GYD per night

Guest favorite

Guesthouse in Brattleboro

4.93 out of 5 average rating, 427 reviews

Mahalo Temple Retreat

Retreat in Mahalo's beautiful, private sound healing temple surrounded by nature, amongst streams, berry bushes, fruit & nut trees, medicinal plants and veggie gardens. We are set back just enough from a main road to find your serenity and yet close enough to civilization for human interaction and trails for hiking. Quiet and peaceful location just a few min off I-91 and just over 2 miles from the center of Brattleboro. A fun and quirky town with art cafes, restaurants, and great shops.

Jul 6 – 13

G$20,140 GYD per night

Guest favorite

Barn in Marlboro

4.95 out of 5 average rating, 263 reviews

The Studio With a View. Bring your dog, too!

Our stylish Studio, a not so tiny Tiny House, is nestled into the Southern Vermont hillside and surrounded by nature. Enjoy the view from the deck, and cozy up in the newly renovated flower barn with a cup of coffee or tea and a great book. Well-mannered dogs are welcome, they will enjoy the fenced-in area right off the deck. Features: efficiency kitchen and dining area, cozy living space, queen-size bed, and a full bathroom. The large covered porch overlooks fields and trees.

Jan 2 – 9

G$29,300 GYD per night

Guest favorite

Cabin in Whitingham

4.96 out of 5 average rating, 111 reviews

The Hideaway Camp

The Hideaway Camp is a very private cabin on a 100 acre property. There are hiking/x country ski trails on the property and close access to the VAST trails. A scenic 20 acre pond for kayack and canoeing and a brook with a rustic cocktail deck overlooking it. the Jacksonville General store is 2 minutes away and it is warm and friendly with all the groceries you might need. The cabin is well stocked for cooking and with high speed internet you can WFH or stream favorite shows.

Nov 15 – 22

G$25,822 GYD per night

Guest favorite

Apartment in Marlboro

4.94 out of 5 average rating, 221 reviews

Shakespeare’s Folly Side Farm and AirBnB.

Located on a gorgeous south-facing hillside in Marlboro, VT, Shakespeare's Folly Side Farm is a light, airy, quiet apartment with stunning views, beautiful gardens, and walking paths. We have friendly goats and dogs, vegetable and flower gardens and a small orchard, with raspberries and blueberries. Free picking in the summer. A magical and inspiring place of rolling lawns and 40 mile views yet so close to the many rich cultural and recreational options in southeast Vermont.

Nov 22 – 29

G$30,206 GYD per night

Guest favorite

Guest suite in Charlemont

4.9 out of 5 average rating, 182 reviews

Unique People & Pet-Welcoming Haven

Your own gracious living space with very well equipped kitchen, private deck, entrance, garden, country roads for dog walks, forests, meadows, mountain streams, stone walls, tranquility. The cottage is attached to the main house but is a "separate" entity and again has its own private entrance as mentioned above. No smoking in the cottage please but on the deck just fine. There is an air purifier that runs 24/7. Wi-Fi signal is strong and reliable. MA Taxpayer ID: 10352662

Dec 6 – 13

G$22,966 GYD per night

Guest favorite

Apartment in Wilmington

4.92 out of 5 average rating, 107 reviews

Walk To Wilmington Village (Reduced Spring Rate)

This charming apartment is on a quiet side road overlooking historic downtown Wilmington, Vermont. Hear the church bells nearby while enjoying a relaxing evening on the deck. Take a stroll downtown and visit restaurants, shops, bars, and giftshops. Easy access to Moover, free bus to Mount Snow. Brand new washer/dryer Smart TV with a variety of premium streaming services The entire covered porch, side porch, and the yard on that side is all private and for you to enjoy.

Jul 4 – 11

G$25,462 GYD per night

Guest favorite

Guest suite in Wilmington

4.92 out of 5 average rating, 712 reviews

Architectural GuestSuite

The Guest Suite is located on the first floor of an architectural studio in historic Wilmington, Vermont. Please enjoy the piano, drums, and art supplies! The Guest Suite is both UNIVERSALLY ACCESSIBLE, TOBACCO FREE, and ANIMAL FREE due to allergies in our family. LineSync Architecture staff will be working from 8:30am - 5ish upstairs, and once in a while on the weekends. When guests are in we try to be super sensitive and quiet, but footsteps will be heard!

Jul 30 – Aug 6

G$24,560 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Whitingham vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Whitingham's top sights

Jacksonville General Store Inc.5 locals recommend

Sprague & Son Maple3 locals recommend

Spoonwood Cabin Creamery10 locals recommend

Other great vacation rentals in Whitingham

Guest favorite

Apartment in Marlboro

4.95 out of 5 average rating, 112 reviews

Southern Vermont Sweet Spot

Mar 23 – 30

G$20,270 GYD per night

Guest favorite

Apartment in Greenfield

4.96 out of 5 average rating, 267 reviews

Mohawk Trail View/ private apt. no cleaning Fee

Jul 24 – 31

G$21,897 GYD per night

Guest favorite

Apartment in Bennington

4.93 out of 5 average rating, 527 reviews

The Octopus's Garden

Jun 17 – 24

G$20,355 GYD per night

Guest favorite

Cabin in Savoy

4.98 out of 5 average rating, 186 reviews

The Camp - 20 Minutes to Berkshire East!

Sep 29 – Oct 6

G$23,831 GYD per night

Guest favorite

Guest suite in Brattleboro

4.94 out of 5 average rating, 518 reviews

Charming studio in renovated 19th century church.

Dec 21 – 28

G$19,477 GYD per night

Guest favorite

Chalet in Dover

4.93 out of 5 average rating, 264 reviews

A charming VT chalet

Mar 12 – 19

G$34,323 GYD per night

Guest favorite

Home in Whitingham

4.97 out of 5 average rating, 61 reviews

Gorgeous farmhouse beautiful view pond/mountains

Sep 5 – 12

G$35,293 GYD per night

Guest favorite

Cabin in Whitingham

5.0 out of 5 average rating, 14 reviews

The Green Mountain Roost (Dogs Welcome!)

Sep 13 – 20

G$37,838 GYD per night

Show all

Quick stats about vacation rentals in Whitingham

Total rentals
30 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.4K reviews
Nightly prices starting at
G$16,711 GYD before taxes and fees

Frequently Asked Questions

Do house rentals in Whitingham have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Whitingham. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Whitingham?
Experience the best of Whitingham with our house rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for House Rentals in Whitingham?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a kitchen, over 20 homes with free parking, over 20 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Whitingham have wifi?
Absolutely! We offer over 20 house rentals with wifi in Whitingham. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Whitingham?
Whitingham has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Whitingham have free parking?
Absolutely! We offer over 20 house rentals with free parking in Whitingham. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Whitingham?
Yes! Work meets play with ease at over 10 vacation rentals in Whitingham featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Whitingham?
Four-legged friends are welcome in Whitingham. Choose from more than 10 vacation rentals for guests traveling with pets.

Vacation rentals in Whitingham

Top-rated vacation rentals in Whitingham

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Whitingham vacation rentals

Stay near Whitingham's top sights

Other great vacation rentals in Whitingham

Apartment in Marlboro

Apartment in Greenfield

Apartment in Bennington

Cabin in Savoy

Guest suite in Brattleboro

Chalet in Dover

Home in Whitingham

Cabin in Whitingham

Quick stats about vacation rentals in Whitingham

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Whitingham have a kitchen?

How much does it cost to stay in house rentals in Whitingham?

What are the most popular amenities for House Rentals in Whitingham?

Do house rentals in Whitingham have wifi?

Are there family-friendly vacation rentals in Whitingham?

Do house rentals in Whitingham have free parking?

Are there vacation rentals with a dedicated workspace in Whitingham?

Are there pet-friendly vacation rentals in Whitingham?

Destinations to explore