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Whitingham Vacation Rentals

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Vacation Rentals in Whitingham

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Terrace/patio
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
9.6 out of 10, Exceptional, (39)
"My friends and I book this mansion for our annual getaway and it has become so dear to us. "
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Interior
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, (35)
"We read all reviews before we booked and everything said was absolutely accurate. We had a perfect get-away, walking into a beautifully designed and appointed space. Chris is a super host, readily available and responsive to all question and offering fantastic advice on local offerings. Our days started with the best breakfast sandwich ever at his country store, the days ended with extraordinary sunsets and sitting in the hot tub looking at the endless stars. We brought our couch potato dog and...
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!
Property grounds
Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!
10.0 out of 10, Exceptional, (26)
"The house was perfect for a group of five of us. The kitchen and grill were great for our culinary needs. Thanks for letting us stay!"
Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!
Seasons On Mount Snow - Ski-in/Ski-out
Indoor pool, a heated pool
Seasons On Mount Snow - Ski-in/Ski-out
9.8 out of 10, Exceptional, (155)
"The property was very clean beautiful location , definitely be Book there again "
Seasons On Mount Snow - Ski-in/Ski-out
Bear Creek Cabin
Exterior
Bear Creek Cabin
10.0 out of 10, Exceptional, (18)
"Everything was as described, clean and comfortable with good amenities. Lots of thoughtful extras in the house that made our stay very enjoyable."
The price is $604
includes taxes & fees
$541 per night
Oct 1 - Oct 2
Bear Creek Cabin
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
10.0 out of 10, Exceptional, (209)
"We loved our stay at the converted barn! It was completely private and super quiet. The hot tub was great, and I have never seen so many stars in my life! The house was very beautiful and felt like a home, we loved taking a look at all the decor. By the time our trip was coming to an end, we were super sad... we never wanted to leave! I would definitely return to Lars' place!! "
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Property grounds
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, (38)
"A friend and I stayed at this location for a few days in the autumn. Everything was as listed and it was perfect for our getaway. I would highly recommend this place for anyone I know looking for a quiet and quaint place to stay!"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
TV, fireplace, DVD player, books
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, (52)
"We had a fabulous time. "
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
Mount Snow's Best View - Sleeps 8-10
Fridge, microwave, oven, stovetop
Mount Snow's Best View - Sleeps 8-10
10.0 out of 10, Exceptional, (43)
"The property has great views of the mountain, the place was clean and offered plenty of space. It is located near plenty of restaurant's and across the street from Mt. Snow. The clubhouse is new and was a nice bonus to use. "
Mount Snow's Best View - Sleeps 8-10
Wilmington Family Escape! King Beds, Sleeps 13, Air hockey, Nerfgun Fun
Property grounds
Wilmington Family Escape! King Beds, Sleeps 13, Air hockey, Nerfgun Fun
10.0 out of 10, Exceptional, (38)
"We were 10 family members attending a cousins wedding. We loved all the sleeping spaces the kitchen and the bathroom rooms were updated clean and nice. We could walk to town for breakfast or across the street for forgotten items. The neighborhood isn’t beautiful but once inside the house or looking at the backyard- it’s easy to forget that "
The price is $730
includes taxes & fees
$646 per night
Sep 29 - Sep 30
Wilmington Family Escape! King Beds, Sleeps 13, Air hockey, Nerfgun Fun
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Exterior
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, (122)
"My partner and I were in MA to drop our eldest at Smith College for their first year. We chose Flight's End for the location and the fact that we were allowed to bring our pups with us. It was incredibly peaceful and just what we needed during an otherwise emotional time with such a big transition for our family. "
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Perfect for Leaf Peeping w/Bar Room, Hot Tub
Interior
Perfect for Leaf Peeping w/Bar Room, Hot Tub
9.8 out of 10, Exceptional, (10)
"We had 15 members of my family in this old house. Another 5 at another VRBO , and 4 others that joined us all day Saturday. Good weather and the annual recognition of the Battle of Bennington was a wonderful surprise The house needs many repairs. The kitchen was a big disappointment "
Perfect for Leaf Peeping w/Bar Room, Hot Tub
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Golf
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
10.0 out of 10, Exceptional, (103)
"We have 2 dogs who travel with us. So renting pet friendly homes is a much better option than a hotel room. The house was clean, comfortable, and the fenced in yard was great for our dogs. Nice big bath towels (my favorite) and a nicely stocked kitchen made staying at this house very enjoyable. An added bonus were two sets of dog-loving neighbors who came out to greet us and say hello to our pups. Thanks Julie for providing a welcoming place to stay for our weekend getaway."
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Property grounds
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.6 out of 10, Excellent, (20)
"Good Condo in a great location"
The price is $280
includes taxes & fees
$251 per night
Oct 1 - Oct 2
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Property grounds
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
9.0 out of 10, Wonderful, (41)
"We had a group of thirty-four people for a family vacation and had a blast. The host and the housekeeper were tremendously responsive to any small issues we had over the first few days. The kitchen was well stocked but could use more mugs for coffee/tea and additional forks for larger groups and the tea bags were past the best before date and should be replaced. Twelve bedrooms, each with their own bathroom was great. The pool, hot tubs, ping pong table, pool table, tennis court, and fire pit...
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Property grounds
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
10.0 out of 10, Exceptional, (208)
"Superb views of the Vermont Mountains and spacious property made this a location my family would love to revisit! We booked Tony's home rather last minute as a Labor Day retreat for my family and several friends, we were blown away by the facilities on-site and closeness to the lake. The kids loved the game room, bicycles, and even tried kayaking by themselves. As a note to perspective renters, this property is about a 1,000ft walk to the lake from the hill the house is based on. Older renters...
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Wilmington Vacation Rental Near Hiking and Skiing!
TV, fireplace, books
Wilmington Vacation Rental Near Hiking and Skiing!
9.8 out of 10, Exceptional, (11)
"Beautiful cabin! Right in the middle of nature with plenty of things to do nearby. Host was exceptional!"
Wilmington Vacation Rental Near Hiking and Skiing!
Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym
1 bedroom, iron/ironing board, internet, bed sheets
Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym
8.0 out of 10, Very Good, (2)
"My stay with a friend at this location was extremely pleasant overall; the home was well furnished, stocked, and the surroundings of rural Vermont were beyond gorgeous. The interior was very well cleaned when I arrived, though my friend and I very quickly noticed that there was a distinct septic-like odor in the house's central hallway area and the home's exterior (walking up to the entryway, etc). This smell persisted throughout the duration of the stay, but was most noticeable on days where...
Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym
Dog-friendly chalet cabin with valley view, deck, and private hot tub
TV
Dog-friendly chalet cabin with valley view, deck, and private hot tub
7.2 out of 10, Good, (14)
"We had a great weekend staying here. The projector and hot tub were awesome amenities. There was a snow storm right before we arrived and the roads were clear and the driveway was plowed. We had a great experience and would stay here again!"
Dog-friendly chalet cabin with valley view, deck, and private hot tub
Green Mountain Modern House: iconic modern getaway
Exterior
Green Mountain Modern House: iconic modern getaway
Green Mountain Modern House: iconic modern getaway
Don't see what you're looking for?
See all available properties in Whitingham
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.
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Other types of properties in Whitingham you may be interested in

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Interior
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, (35)
"We read all reviews before we booked and everything said was absolutely accurate. We had a perfect get-away, walking into a beautifully designed and appointed space. Chris is a super host, readily available and responsive to all question and offering fantastic advice on local offerings. Our days started with the best breakfast sandwich ever at his country store, the days ended with extraordinary sunsets and sitting in the hot tub looking at the endless stars. We brought our couch potato dog and...
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Terrace/patio
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
9.6 out of 10, Exceptional, (39)
"My friends and I book this mansion for our annual getaway and it has become so dear to us. "
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Hotel Downstreet
Hypo-allergenic bedding, laptop workspace, blackout drapes
Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, (1004)
"This hotel is immaculate. We were pleasantly surprised to have room cleaning each day of our stay. The staff is super friendly and efficient. One small disadvantage, the noise from the street traffic was loud in our room. We would definitely stay there again."
The price is $125
includes taxes & fees
$112 per night
Sep 29 - Sep 30
Hotel Downstreet
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.

Frequently asked questions

Can I find vacation rentals in Whitingham?

Yes, we offer vacation rentals near popular local attractions in Whitingham, or you can select a more secluded option if you'd like a relaxing place to stay. Whitingham is known for its wineries and parks.

What's the top vacation rental in Whitingham?

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating : Visitors give good reviews to this Whitingham vacation home rental, which is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a spa tub so you can immerse yourself in your vacation. Another good choice for your trip to Whitingham is Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included.

How many vacation rentals are there in Whitingham?

Expedia has 15 vacation rentals for your stay in Whitingham.

What’s there to see and do in Whitingham?

Harriman Reservoir and Deerfield River are a couple of lovely local spots to get outside and enjoy nature. Mount Snow and Hogback Mountain Conservation Area are a couple of places you'll find in the larger area.

What are vacation rentals like in Whitingham?

Vacation rentals are privately owned accommodations you can reserve for a few days or a quick weekend in Whitingham. Vacation rentals feature extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family gatherings.