Whitingham Vacation Homes

A rural landscape with rolling hills, a winding road, and autumn-colored trees.

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Our top choices for Whitingham holiday homes

An aerial view of a house surrounded by a forest with autumn foliage.

1. Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11

Whitingham

Jonathan

HK$4,026 total

includes taxes & fees

2 Nov - 3 Nov

A cozy interior with a wooden ceiling, a large window, and a table with chairs.

2. VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

Wilmington

Natalie

HK$4,490 total

includes taxes & fees

18 Nov - 19 Nov

A deck with two wicker chairs and a string of lights against a backdrop of trees and a sunset.

3. The Eagles Wing at The CHM - Private Apartment

Dover

Ava M.

HK$1,490 total

includes taxes & fees

23 Oct - 24 Oct

A bedroom with a wooden headboard, a bed with patterned bedding, and a framed picture on the wall.

4. MtSnow* HotTub* Pool * AirHockeyPingPong Darts

Wilmington

HK$5,085 total

includes taxes & fees

21 Oct - 22 Oct

A bedroom with a bed, bedside tables, a window, and a radiator.

5. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

Woodford

Dana W.

HK$3,464 total

includes taxes & fees

2 Nov - 3 Nov

A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

6. Greylock Cabin

Florida

Margaret M.

HK$3,600 total

includes taxes & fees

17 Nov - 18 Nov

A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

7. Walk To Town, Hottub, Firepit, Games, Mt Snow

Wilmington

Jeremy P.

HK$6,057 total

includes taxes & fees

21 Oct - 22 Oct

A spacious indoor area with multiple wooden tables and green chairs, large windows offering a view of a snowy mountain, and a stone fireplace with a fire.

8. Modern Mount Snow Gnarvana - Steps to Carinthia

Dover

Lynn B.

HK$3,282 total

includes taxes & fees

21 Oct - 22 Oct

A modern interior with large windows, a wooden ceiling, and a cozy seating area.

9. Stunning Glass House nestled in the Vermont wilderness!

Guilford

Chris O.

HK$3,986 total

includes taxes & fees

8 Nov - 9 Nov

A two-story house with a porch, surrounded by trees and snow.

10. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Bennington

Malika R.

A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

11. Private bed with En-suite bathroom Marigold Room

Shelburne Falls

HK$1,622 total

includes taxes & fees

9 Nov - 10 Nov

A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

12. Cozy Vermont Tiny Home Get Away

Brattleboro

HK$816 total

includes taxes & fees

4 Nov - 5 Nov

A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

13. 5BR Berkshire Home Mins To The Mountain

Charlemont

Jason F.

HK$5,705 total

includes taxes & fees

21 Oct - 22 Oct

A wooden barrel structure with a staircase and railing, surrounded by a forest.

14. 10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK

Dover

Connor S.

HK$5,368 total

includes taxes & fees

16 Nov - 17 Nov

A kitchen with white cabinets, a wooden dining table, and pendant lights.

15. A roomy remodeled retreat close to MassMoCA

North Adams

Diane

HK$3,769 total

includes taxes & fees

30 Oct - 31 Oct

A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

16. Lovely 2nd Floor Apartment

Greenfield

Jane P.

HK$1,964 total

includes taxes & fees

25 Oct - 26 Oct

A hallway with wooden flooring, white walls, and a bed in the background.

17. Cozy private 2 bed apartment in Shelburne Falls

Shelburne Falls

maureen

HK$3,272 total

includes taxes & fees

26 Oct - 27 Oct

A wooden kitchen with a central island, bar stools, and a dining table with chairs.

18. Cozy Home in Pownal VT

Pownal

Jeri R.

HK$1,609 total

includes taxes & fees

21 Oct - 22 Oct

A modern kitchen with a built-in fireplace, wine storage, and a dining area with wooden furniture.

19. Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Dover

jim f.

HK$9,254 total

includes taxes & fees

30 Oct - 31 Oct

A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

20. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Williamstown

Michelle B.

HK$4,856 total

includes taxes & fees

3 Nov - 4 Nov

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Top Whitingham Hotel Reviews

Grand Summit Resort, A Vail Resorts Property

10/10 Excellent

"The hotel was built in the 1990’s per the concierge, which surprised us, as it is so well maintained that it seems much newer! We booked a king bed room with (small) balcony. Our only complaint would be the bathroom toilet situation. Toilet is very small and way too close to the door…a very awkward setup, especially trying to get into the shower. The tub and shower however seemed completely new. Very nice! The room is quite large and the bed was very comfortable. I’m only 4’10” so it was a high hurdle for me, so I made up the couch bed and slept there. I usually bring a small folding stool but forgot it, so the couch bed was a nice option…it seems to be new and was comfortable. The first night we ate at the hotel restaurant and everything was very tasty, especially the Brussel sprouts and salmon. We were celebrating my husband’s birthday weekend, and brought wine but had to drink from coffee mugs as the hotel is “green” so no cups in the room. We snagged a couple cups from the restaurant for our second night. 😊 Also there’s no mini fridge. We had breakfast twice at 1MTN restaurant, which we highly recommend! Second night we had dinner at “Ten Tables”…their Berkshire Pork Chop was PHENOMENAL. 3rd night we drove down to Wilmington to “The Anchor”…every single thing was delicious! We had a superb weekend!"

The Porches Inn at Mass MoCA

10/10 Excellent

"The porches Inn was such a lovely cozy place to stay. What we loved: beds were so comfortable and crisp. Thoughtful touches. Very clean and environmentally sustainable. The stainless steel water bottles were great to have using them to refill water that were placed throughout the property. The breakfast each morning was the same however, it was fresh with several options . I had a lox bagel each day with fresh squeezed orange juice and they have non dairy/GF options as well! The coffee is outstanding. They source from a local coffee shop. We couldn’t get enough of it What we thought could be better : Prices listed on their merchandise would be a good choice . I went to buy the water bottle they sell and had no idea it cost $40! Should have asked but I would never assume they would charge so much. We thought the staff seemed grumpy or didn’t seem they wanted to be there. Smiles and hellos were absent throughout our 4 day /3 night stay. A little more friendly vibe would have been nice as it was a hotel staffed property that caters to guests. Other than that, we loved it. The price was well suited for what we received and the location was fabulous. I also enjoyed how they listed all available hikes on thier boards making it easy to pick the one we wanted for the day."

Hideaway Inn Mt. Snow

8/10 Good

"It was a tablet check in which was fairly easy but sends the room number and access code to your e mail address . The rooms were clean and tidy. Free hot drinks in an area on a lower floor. Check out didn’t work on the tablet, so used the telephone. Nobody answered that call, but a member of staff appeared and said everything was fine and we could leave. Diving distance to local restaurants and there were numerous. The gondola was close by, although we didn’t go to the top because it was raining hard and didn’t think we would see much."

Hampton Inn Brattleboro

10/10 Excellent

"Excellent place to stay, clean seems new, has small pool and water bath (kind of like jacuzzi) clean room, staff is nice and friendly. Includes breakfast and all day coffee or hot water to make teas (that is a must for me) as I need to make me teas few times a day. Would recommend for sure. If it was cheaper than it would really be off the charts but I will not include that into the review."

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