Whitingham Holiday Houses

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

Whitingham

Jonathan

includes taxes & fees

28 Sept - 29 Sept

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

Jack & Heather G.

includes taxes & fees

13 Sept - 14 Sept

A room with a wooden bed, a mirror, and a window.

3. MtSnow* HotTub* Pool * AirHockeyPingPong Darts

Wilmington

includes taxes & fees

15 Sept - 16 Sept

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

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

Wilmington

Nicholas G.

includes taxes & fees

13 Sept - 14 Sept

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

5. Private bed with En-suite bathroom Marigold Room

Shelburne Falls

includes taxes & fees

13 Sept - 14 Sept

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

6. Lovely 2nd Floor Apartment

Greenfield

Christa B.

includes taxes & fees

13 Sept - 14 Sept

A two-story house with a red roof, a front porch with a railing, and a gravel driveway.

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

Woodford

includes taxes & fees

13 Sept - 14 Sept

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

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

Bennington

Malika R.

includes taxes & fees

13 Sept - 14 Sept

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

9. Cozy Home in Pownal VT

Pownal

Jess M.

includes taxes & fees

24 Sept - 25 Sept

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

10. Cozy private 2 bed apartment in Shelburne Falls

Shelburne Falls

maureen

includes taxes & fees

14 Sept - 15 Sept

A wooden staircase leading to a cabin with a balcony, surrounded by trees.

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

Wilmington

Alex B.

includes taxes & fees

9 Oct - 10 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.

12. Modern Mount Snow Gnarvana - Steps to Carinthia

Dover

Lynn B.

includes taxes & fees

14 Sept - 15 Sept

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

13. The Greylock Cabin

Florida

Margaret M.

includes taxes & fees

7 Oct - 8 Oct

A red house with a porch, surrounded by a grassy yard and trees.

14. 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

includes taxes & fees

13 Sept - 14 Sept

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

15. 5BR Berkshire Home Mins To The Mountain

Charlemont

Jason F.

includes taxes & fees

14 Sept - 15 Sept

A room with wooden walls, a window with a view of the sky and greenery, a hanging macrame wall decoration, and a vase with flowers on the windowsill.

16. Peaceful getaway at birds of a feather

Shaftsbury

Michaela J.

includes taxes & fees

15 Sept - 16 Sept

A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

17. Spacious 5BR w/ Hot Tub & Games

Colrain

Staci M.

includes taxes & fees

14 Sept - 15 Sept

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

18. A roomy remodeled retreat close to MassMoCA

North Adams

Jennifer O.

includes taxes & fees

15 Sept - 16 Sept

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

19. Stunning Glass House nestled in the Vermont wilderness!

Guilford

Chris O.

includes taxes & fees

24 Sept - 25 Sept

A pathway through a forest with autumn leaves and a wooden bridge.

20. Experience Vermont’s Fall Magic at here at the Lemondrop

Dover

Alexander H.

includes taxes & fees

14 Sept - 15 Sept

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Top Whitingham Hotel Reviews

Inn At Mount Snow

10/10 Excellent

"Pretty views, comfortable bed, nice room, pleasant stay."

Latchis Hotel

8/10 Good

"This hotel is a great representation of a niche throw back. Record players in the room. Stacks of records in the hall to enjoy. The lobby is beautiful and they are attached to the movie theatre, which is old school and beautiful to witness. The hotel is in a TERRIBLE AREA and in fact Brattleboro, VT has an extremely large homeless and drug population. I truly feel for the business’ in the town. No foot traffic. We didn’t see one police vehicle at all. Multiple people told us to keep our wits about us if walking at night. The restaurants that we did visit have lovely people and are friendly but the places to see are not worth a visit to this sad town. It’s truly unfortunate too. You have this idea of small town in New England with shops and mom and pop places to eat and this had almost NONE of that."

Hideaway Inn Mt. Snow

10/10 Excellent

"We had a great experience here, well thought out instructions are provided for the electronic check in and room key. No staff (you do not need anyone), very clean and large room. Beautiful property, two very large downstairs living areas with nice amenities (espresso coffee and tea maker), lots of seating and games) and a gorgeous view. Lovely gated on-site pool area. This property is perfect for my dog, who loves to play fetch. Grounds are groomed."

Find out more about Whitingham

Whitingham Holiday Homes information

Number of reviews	328
Accommodation	440 Holiday Homes
Lowest Price	NZ$346
Highest Price	NZ$1,277

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Whitingham holiday 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. MtSnow* HotTub* Pool * AirHockeyPingPong Darts

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