Whitingham, VT Vacation Homes from AED 751

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

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Our top choices for Whitingham vacation homes

1. Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Whitingham

Jonathan

AED 1,901 total

includes taxes & fees

2 Sep - 3 Sep

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

Wilmington

Jack & Heather G.

AED 2,102 total

includes taxes & fees

16 Sep - 17 Sep

3. Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views

Stamford

Donna E.

AED 1,113 total

includes taxes & fees

31 Aug - 1 Sep

Smart TV, fireplace, video games, DVD player

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

Wilmington

Nicholas G.

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

Bennington

Malika R.

AED 1,117 total

includes taxes & fees

26 Aug - 27 Aug

6. Private bed with En-suite bathroom Marigold Room

Shelburne Falls

AED 792 total

includes taxes & fees

31 Aug - 1 Sep

7. New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly

Wilmington

Alex B.

AED 2,681 total

includes taxes & fees

4 Sep - 5 Sep

8. Stunning Glass House nestled in the Vermont wilderness!

Guilford

Chris O.

AED 1,971 total

includes taxes & fees

21 Sep - 22 Sep

9. Lovely 2nd Floor Apartment

Greenfield

Christa B.

AED 751 total

includes taxes & fees

26 Aug - 27 Aug

10. Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont

Noah K.

AED 3,451 total

includes taxes & fees

1 Sep - 2 Sep

11. Cozy Home in Pownal VT

Pownal

Jess M.

AED 757 total

includes taxes & fees

30 Aug - 31 Aug

12. Cozy private 2 bed apartment in Shelburne Falls

Shelburne Falls

AED 1,342 total

includes taxes & fees

2 Sep - 3 Sep

13. Two Brooks Lodge

Bennington

"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...

Hunter

AED 1,447 total

includes taxes & fees

26 Aug - 27 Aug

14. Summer Escape Near Lakes, Trails & Mt Snow

Dover

william k.

AED 1,795 total

includes taxes & fees

26 Aug - 27 Aug

15. 5BR Berkshire Home Mins To The Mountain

Charlemont

Jason F.

AED 2,462 total

includes taxes & fees

26 Aug - 27 Aug

16. The Greylock Cabin

Florida

Anonymous traveler

AED 1,832 total

includes taxes & fees

23 Sep - 24 Sep

17. Peaceful getaway at birds of a feather

Shaftsbury

Aidan K.

AED 913 total

includes taxes & fees

31 Aug - 1 Sep

Coffee/tea maker, fridge, microwave, oven

18. Spacious 5BR w/ Hot Tub & Games

Colrain

Maureen A.

AED 2,401 total

includes taxes & fees

26 Aug - 27 Aug

19. A roomy remodeled retreat close to MassMoCA

North Adams

Jennifer O.

AED 1,781 total

includes taxes & fees

9 Sep - 10 Sep

20. 3 Mi to Mount Snow: Spacious West Dover Home

West Dover

ken g.

AED 2,528 total

includes taxes & fees

26 Aug - 27 Aug

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Top Whitingham Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good

"We have been coming for the last few years. Generally, 4 or 5 times a year. We love the Berkshires. People vote with their feet. It is a good value. We will be back."

Latchis Hotel

8/10 Good

"The room was very clean and the staff was amazing but the proximity of the hotel makes it hard to sleep in the morning. It’s at a very busy intersection, and the train comes through and blasts its horn early in the morning.It is a great place to stay, but if you want to sleep in, it’s not the right place for you."

Hotel Vervana, Trademark Collection by Wyndham

8/10 Good

"The staff was incredibly helpful and the breakfast was homemade not powdered eggs. Down side was the walls were a bit thin. Rooms were well appointed and it’s in a great location. I was there to volunteer for a RAm event and a lot of us stayed there. Next year I would stay there again. Maybe we can get all the RAM volunteers in one building as we have to get up at 4 am"

Hideaway Inn Mt. Snow

10/10 Excellent

"We will definitely return to the Hideaway! We got a text before arrival with our room number and code which was very convenient. The hotel is warm and cozy and beautifully decorated. There is neat stuff to look at everywhere. The 3 floors of common spaces were really cool with a lot to offer, like a water bottle filler and coffee maker. It could use to be cleaned a little more often. When we arrived, the playroom had toys all over the floor and there were sticky drink marks on the bar and crumbs on the coffee table. Someone had crushed the chalk under the dart board and all but 1 of the darts was broken. Regardless, we had a blast playing classic Mario on the arcade game. The living room upstairs was gorgeous, next time we will be sure to use that to play games and maybe watch a movie. We didn’t use the pool because it looked green (we opted to go to the lake instead) but we did make a fire and made s’mores down at one of the fire pits on our second night which was so nice to have. The closet in the hallway to grab towels and such is super convenient and the manager was only a text away if you needed anything. Our room was beautiful and so big. We loved the balcony and the record player in the room was a cool touch my boys had fun listening to. This is a very quiet property with a lot to keep families occupied or just relax and enjoy nature. We had a wonderful stay and when we met the manager she was so sweet! We absolutely loved it and will return for future VT trips."

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Whitingham vacation homes

1. Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

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

3. Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views

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

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

6. Private bed with En-suite bathroom Marigold Room

7. New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly