Winchester Holiday Rentals, New Hampshire: Private House Rentals

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Our top choices for Winchester hotels

A two-story house with a red door, green shutters, and a snow-covered front yard.

1. Centennial House

Northfield

Alan

4.903.199 ₫ total

includes taxes & fees

28 Oct - 29 Oct

A windmill, a row of cabins, and a forest backdrop.

2. Windmill Motel Restaurant

Bernardston

Donna

3.016.913 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A hotel reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.

3. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Lisa

3.729.836 ₫ total

includes taxes & fees

12 Nov - 13 Nov

A hotel with a covered entrance, a clear sky, and a tree in the foreground.

4. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

Timothy

4.094.006 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A bar area with a high ceiling and stained glass windows, bar stools, and a checkered floor.

5. Best Western Plus Keene Hotel

Keene

Ruddy

3.969.473 ₫ total

includes taxes & fees

1 Nov - 2 Nov

The exterior of Latchis Hotel with a prominent entrance, large windows, and potted plants.

6. Latchis Hotel

Brattleboro

Erik

3.983.980 ₫ total

includes taxes & fees

3 Nov - 4 Nov

A modern building with a brick facade and large windows, surrounded by lush greenery and flowers.

7. The Inn At Crumpin Fox

Bernardston

Al

3.247.181 ₫ total

includes taxes & fees

4 Nov - 5 Nov

A hotel lobby with a reception desk, two sofas, a coffee station, and a dining area.

8. Comfort Inn & Suites Brattleboro I-91

Brattleboro

Charlene

3.118.553 ₫ total

includes taxes & fees

22 Nov - 23 Nov

A modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.

9. Hampton Inn & Suites Keene

Keene

Dayle

4.540.708 ₫ total

includes taxes & fees

19 Nov - 20 Nov

A large indoor swimming pool with clear water, surrounded by tiled walls and a ceiling with recessed lighting.

10. Hampton Inn Brattleboro

Brattleboro

Faith

3.117.415 ₫ total

includes taxes & fees

15 Nov - 16 Nov

11. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

Christopher

5.434.716 ₫ total

includes taxes & fees

3 Nov - 4 Nov

A wooden cabin with a thatched roof, accessible via a wooden walkway with railings.

12. Vikings Villages Resort

Guilford

Cecil

5.647.989 ₫ total

includes taxes & fees

28 Oct - 29 Oct

A dock extending into a lake with a grassy area in the foreground and trees in the background.

13. Riverside Hotel, an Ascend Collection Hotel

West Chesterfield

Steve

3.867.397 ₫ total

includes taxes & fees

25 Nov - 26 Nov

A hotel room with two beds, a TV, a desk, and a window with curtains.

14. Days Inn by Wyndham Keene NH

Keene

CHERYL

2.645.848 ₫ total

includes taxes & fees

29 Oct - 30 Oct

A bar area with a dark tiled backsplash, multiple stools, and a variety of bottles and glasses on the counter.

15. Courtyard by Marriott Keene Downtown

Keene

Deborah

5.301.512 ₫ total

includes taxes & fees

3 Nov - 4 Nov

A swimming pool area with lounge chairs and a sunbed, surrounded by windows and doors.

16. Econo Lodge Brattleboro South

Brattleboro

Luis

2.827.424 ₫ total

includes taxes & fees

26 Nov - 27 Nov

A large, white, two-story house with a dark roof, surrounded by lush greenery and a gravel pathway.

17. Inn on Putney Road

Brattleboro

Karla

7.588.644 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A dining area with a table and four chairs, a painting of a covered bridge, and a painting of a red building.

18. The Covered Bridge Inn

Brattleboro

Rick

2.353.200 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A wooden table set with plates, cutlery, and a folded napkin.

19. The Carriage Barn Inn

Keene

Richard

4.507.729 ₫ total

includes taxes & fees

19 Nov - 20 Nov

A hotel with a clock tower, a parking lot, and a well-maintained garden.

20. Black Mountain Inn

Brattleboro

Ron

3.418.808 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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Stay near popular Winchester attractions

Winchester Speedpark

Winchester Speedpark thrills with professionally designed motocross tracks featuring challenging jumps and turns. Experience heart-pounding night races or watch competitors tackle the New England racing circuit.

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Learn more about Winchester

Hike the scenic trails of Pisgah State Park where rangers know which routes offer the best wildlife viewing. Explore the historic city centre district with its charming 19th-century architecture and local shops selling New Hampshire maple products.

See all hotels in Winchester

A snow-covered bridge over a river with a red roof, surrounded by trees and buildings.

Top Winchester Hotel Reviews

Gardner Inn

8/10 Good

"Staff was polite. Good location. Quiet. Comfortable bed."

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent

"It was a restful 3 night stay after a day of exploring. Breakfast was great - great choices each day. Parking was easy and convenient. Staff was great. Gym had everything I needed. Would have liked to use the pool, but the heater was out of order. It was still available for the brave hearts. Room was clean. Overall - exceeded my expectations."

The Colonial Hotel

8/10 Good

"This is a dated, solid 3-star hotel. The interior finishes all need a serious refresh. I was on the ground floor in a nice room, but the Wi-Fi was terrible and they stuck me down by the mechanical plant and housekeeping offices. Normally not a bid deal but they left the doors open to the mechanical room the entire time I was in my room. They also need to update the quality and number of WAPs. They were confused when I asked if they had a "business center" because they don't. Given the quality of the Wi-Fi in my room, it would've been nice if they had one.😊 The Colonial Grille is awesome; it is a shining star for this somewhat tired hotel. The restuarant/bar staff are awesome, and the food is good American fare. The bar is a lot of fun, and it's big. This is a local destination for weddings. I was there from Friday to Sunday in late October and I think there were not less than 3 weddings."

Latchis Hotel

8/10 Good

"It’s located with restaurants within walking distance. It is well maintained for a historic hotel with probably about 15 steps in the lobby before you get to the elevator. It was noisy some nights due to being in the city and having residents living life. Staff was wonderful. Again location was great to see Buffalo—Niagara is 20 min away, Botanic Garden and Eternal Flame about the same. We enjoyed our stay."

Days Inn by Wyndham Keene NH

8/10 Good

"Clean comfortable room with a comfortable bed. I didn’t like the smell of whatever cleaning product they used, it was a bit bit strong let the kind you used to cover up something. Was this recently a smoking hotel? Also I missed an cycle in the fitness center, although the machines that were there seemed to work well. All in all it’s about what you would expect for a moderately priced hotel in New Hampshire during leaf peeper season."

More cheap stays in Winchester

The Putney Inn

57 Putney Landing Rd Putney VT

2.174.941 ₫

2.392.436 ₫ total

28 Oct - 29 Oct

includes taxes & fees

8.4/10 Very good! (1,003 reviews)

Hotels in Winchester with star rating

Frequently asked questions

What's the weather like in Winchester?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winchester are January, March, February and November, with each month seeing an average of 26 cm of snowfall.

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Find hotels in Winchester, NH from 1.961.711 ₫

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Our top choices for Winchester hotels

1. Centennial House

2. Windmill Motel Restaurant

3. Keene Elm City Hotel, an Ascend Collection Hotel

4. Holiday Inn Express Hotel & Suites Brattleboro by IHG

5. Best Western Plus Keene Hotel

6. Latchis Hotel

7. The Inn At Crumpin Fox

8. Comfort Inn & Suites Brattleboro I-91

9. Hampton Inn & Suites Keene

10. Hampton Inn Brattleboro

11. Fairfield Inn & Suites by Marriott Keene Downtown

12. Vikings Villages Resort

13. Riverside Hotel, an Ascend Collection Hotel

14. Days Inn by Wyndham Keene NH

15. Courtyard by Marriott Keene Downtown

16. Econo Lodge Brattleboro South

17. Inn on Putney Road

18. The Covered Bridge Inn

19. The Carriage Barn Inn

20. Black Mountain Inn

Stay near popular Winchester attractions

Winchester Speedpark

Learn more about Winchester

Top Winchester Hotel Reviews

Gardner Inn

More cheap stays in Winchester

The Putney Inn

Hotels in Winchester with star rating

Frequently asked questions

Explore a world of travel with Expedia

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