Winchester Holiday Rentals, New Hampshire: Private House Rentals

A snow-covered town with a river running through it, surrounded by mountains and trees.

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Our top choices for Winchester hotels

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

A gazebo with a red roof and white walls, surrounded by trees and a brick building.

A conference table set for a meeting with chairs and folded red napkins.

A brick building with a red awning and a sign that reads "The Inn."

1. The Inn At Crumpin Fox

Bernardston

Alan

Rp1.836.311

Rp2.051.147 total

includes taxes & fees

28 Sept - 29 Sept

A bedroom with a geometric-patterned headboard, a bed with a textured white duvet, two pillows, a bedside table with a clock, and a potted plant.

A grassy area with picnic tables and a clock tower.

A large, single-story building with a central entrance and a covered walkway.

A room with a round table and two leather chairs, a window with curtains, and a view of a parking lot outside.

2. Windmill Motel Restaurant

Bernardston

Dan

Rp2.296.060

Rp2.564.699 total

includes taxes & fees

28 Sept - 29 Sept

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

A building entrance with a white door, number 959, and a small porch area decorated with pumpkins, flowers, and scarecrows.

A swimming pool with lounge chairs and a covered umbrella.

A cozy reading area with wooden chairs, a table with newspapers, and potted plants.

3. Black Mountain Inn

Brattleboro

"Absolutely spotless room, the bedding was amazing, the beds were super comfortable. The people were the nicest people ever and we enjoyed them very much. We had a wonderful stay in Vermont. They advised us on where to dine, at the Marina and it was spot on amazing. We had breakfast at The Porch in the morning and the lovely girl even called to make sure they were open before we drove there. We had amazing food there as well."

Denise

Rp2.719.466

Rp2.991.413 total

includes taxes & fees

28 Sept - 29 Sept

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

A modern dining area with a large table and chairs, a kitchen in the background, and a stone accent wall.

A compact hotel room with a kitchenette, a sofa, a small table, and a window with curtains.

A lobby with wooden paneling, a fireplace, and two green armchairs.

4. Hampton Inn Brattleboro

Brattleboro

Francesca

Rp2.865.912

Rp3.152.503 total

includes taxes & fees

28 Oct - 29 Oct

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

A hotel room with two beds, a nightstand, a lamp, a painting of a cabin, and a door.

A multi-story motel with a parking lot, several vehicles parked, and a tree in the foreground.

A reception area with a stone counter, wooden reception desk, and a red carpet.

5. The Covered Bridge Inn

Brattleboro

VINCENT JOEL

Rp2.165.547

Rp2.382.173 total

includes taxes & fees

28 Sept - 29 Sept

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

A covered bridge with a stone foundation, surrounded by lush greenery and a well-maintained lawn.

A hotel lobby with a reception desk, seating area, and a large window.

A banquet hall with round tables, chairs, and a staircase.

6. Latchis Hotel

Brattleboro

jeffrey

Rp2.233.220

Rp2.456.542 total

includes taxes & fees

28 Sept - 29 Sept

A cozy living room with a fireplace, a coffee station, and a view of the outside.

A hotel room with a sofa, a coffee table, a desk with a telephone, a mirror, and a television.

A motel with multiple floors, each with balconies and windows.

A hotel room with two beds, a desk, a chair, a television, a dresser, and a door leading to a bathroom.

7. Colonial Motel

Brattleboro

Alida

Rp1.579.045

Rp1.736.949 total

includes taxes & fees

28 Sept - 29 Sept

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

A hotel lobby with a reception desk, seating area, and a wall with framed pictures.

An indoor swimming pool with a tiled deck, safety signs, and a few chairs.

A hotel room with a sofa, a coffee table, a chair, a desk, and a lamp.

8. Comfort Inn & Suites Brattleboro I-91

Brattleboro

John

Rp2.692.074

Rp2.961.280 total

includes taxes & fees

25 Oct - 26 Oct

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

A two-story building with a porch, a sign indicating guest rooms, and an American flag.

A cozy room with a wooden floor, a rocking chair, a blue armchair, a bookshelf, and a globe on a table.

A corner room with wooden flooring, a wooden table, and four chairs. Large windows with curtains are visible, offering a view of a green landscape and a red deck outside.

9. The Carriage Barn Inn

Keene

Jonathan

Rp2.818.934

Rp3.058.544 total

includes taxes & fees

28 Sept - 29 Sept

A spacious lobby with a reception desk, seating area, and a modern ceiling light fixture.

A spacious lobby with a large flat-screen TV, modern seating, and a large window with a cityscape view.

A hotel entrance with a modern design, featuring a prominent entrance canopy and stone pillars.

A spacious lobby with modern furniture, a large digital map display, and a high ceiling with geometric lighting.

10. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

Daniel

Rp3.204.637

Rp3.525.101 total

includes taxes & fees

25 Oct - 26 Oct

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

A modern kitchen with wooden cabinets, a coffee machine, a fruit juice dispenser, and a refrigerator.

An indoor swimming pool with clear blue water, a lifebuoy, and a few lounge chairs.

A modern fitness center with cardio machines, weightlifting equipment, and a large mirror.

11. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Kristin

Rp2.219.972

Rp2.408.670 total

includes taxes & fees

27 Oct - 28 Oct

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

A reception area with a black marble counter, wooden cabinets, and a 'Staff Only' door.

A Days Inn with a brick facade, a central entrance, and a parking lot.

A conference room with a black table, wooden chairs, a mounted TV, and a decorative mirror.

12. Days Inn by Wyndham Keene NH

Keene

CHERYL

Rp1.612.881

Rp1.749.976 total

includes taxes & fees

27 Oct - 28 Oct

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

A red building with white trim, surrounded by lush greenery and fruit trees.

A group of women in formal attire standing in a garden with a house in the background.

A golf course with a brick pathway, wooden boxes, and a tee box.

13. Centennial House

Northfield

Alan

Rp3.213.194

Rp3.396.346 total

includes taxes & fees

29 Sept - 30 Sept

An indoor swimming pool with clear water, surrounded by windows with a view of trees.

A hotel lobby with a fireplace, seating area, and large windows.

A hotel with a large entrance, a sign reading 'Hampton Inn & Suites,' and a parking lot.

A breakfast area with a sign reading 'HAPPY BREAKFAST STARTS HERE.'

14. Hampton Inn & Suites Greenfield

Greenfield

Pamela

Rp3.802.239

Rp4.247.101 total

includes taxes & fees

5 Oct - 6 Oct

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

A wooden interior with a fireplace, a staircase, and a dining area.

A rustic wooden cabin with a thatched roof, a stone wall, and a wooden staircase leading to a balcony.

A cozy room with a wooden wall, a red sofa, a small table with a bottle, a book, and a plant.

15. Vikings Villages Resort

Guilford

Cecil

Rp2.468.800

Rp2.879.363 total

includes taxes & fees

25 Oct - 26 Oct

A sign for The Putney Inn, a restaurant and motel, with a friendly welcome message and floral decorations.

A motel with a parking lot, a covered walkway, and a staircase leading to the entrance.

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

A grassy field with a playground and trees in the background.

16. The Putney Inn

Putney

JANE

Rp1.506.537

Rp1.657.102 total

includes taxes & fees

25 Oct - 26 Oct

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

A modern hotel with a clear entrance, a parking area, and a sign indicating a 11' clearance.

A hotel suite shop with shelves stocked with snacks and sundries, a refrigerated display case, and a sign indicating 24-hour availability.

A reception area with a 'Welcome to the Granite State' sign, a reception desk, and a well-organized suite shop.

17. Hampton Inn & Suites Keene

Keene

sheri

Rp2.466.317

Rp2.675.954 total

includes taxes & fees

25 Oct - 26 Oct

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

A gazebo with a white fence and a blue roof, surrounded by a well-maintained lawn, with a brick building in the background.

A covered outdoor area with a wooden deck, white railings, and string lights.

A spacious lobby with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

18. Best Western Plus Keene Hotel

Keene

Ruddy

Rp2.488.517

Rp2.700.130 total

includes taxes & fees

25 Oct - 26 Oct

A bar area with a dark wooden bar, multiple bar stools, and a large screen displaying the hotel name.

A bar area with a fireplace, seating, and a TV.

A hotel room with a brick wall, a large bed with white bedding, a flat-screen TV, and a desk with a lamp.

19. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

Caroline

Rp3.469.601

Rp3.764.517 total

includes taxes & fees

25 Oct - 26 Oct

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

A spacious bedroom with a large bed, a desk, and a television.

A building with a large balcony overlooking a body of water, a bridge in the foreground, and trees with autumn foliage.

A spacious living room with a large window, a patterned rug, and multiple seating options including a sofa and armchairs.

20. Riverside Hotel, an Ascend Collection Hotel

West Chesterfield

Jason

Rp3.206.427

Rp3.478.974 total

includes taxes & fees

18 Oct - 19 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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New England Sweetwater Farm & Distillery

This rustic distillery crafts award-winning spirits using locally sourced ingredients. Sample their unique vodkas and whiskies while learning about the distillation process in a warm space adorned with reclaimed wood.

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Cass Pond

This serene 54-acre pond in Richmond offers peaceful fishing for bass, pickerel, and perch. Bring your own gear and a valid New Hampshire fishing licence to fully enjoy this tranquil natural retreat.

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Richmond Wildlife Manangement Area

This protected wilderness features diverse New Hampshire ecosystems across forests, wetlands, and meadows. Explore marked trails for wildlife viewing, especially during spring migration or autumn's foliage display.

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Barden State Wildlife Management Area

This serene wildlife reserve in New Hampshire offers undisturbed natural landscapes for wildlife observation. Bring binoculars for spotting native species while exploring the peaceful trails during spring through fall.

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Loring Field

Explore the great outdoors at Loring Field, a lovely green space in Winchester. While you're in the area, stroll along the lakeside.

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Bennett Gorge

This secluded woodland trail winds alongside a brook to the remnants of an historic mill. Explore Richmond's industrial past while enjoying the tranquil sounds of flowing water and forest solitude.

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Conant Public Library

This historic 1892 library houses Winchester's heritage collection, including one of New England's earliest pipe organs. Browse artefacts or research local history with help from knowledgeable staff.

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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

Best Western Plus Keene Hotel

10/10 Excellent

"Great"

Days Inn by Wyndham Keene NH

10/10 Excellent

"I booked at the last minute for an unplanned visit and was pleasantly surprised by the accommodations for the price."

Gardner Inn

10/10 Excellent

"Room was remodeled. Very nice. Bathroom was decent and got the job done."

Holiday Inn Express Hotel & Suites Brattleboro by IHG

10/10 Excellent

"Hotel was impeccably clean felt brand new. We stayed in a double room, which was perfect to separate bedroom areas connected that share a bathroom perfect for a family."

Deerfield Inn

10/10 Excellent

"Charming well run inn. Staff was wonderful and everything we had from Champneys was delicious. Our room was spacious and very comfortable. My only small "complaint" is that the dining room was overly bright. Putting some of the lights on dimmers would make the entire experience nicer and more cozy, Bar area was perfect and they make good drinks too!"

The Colonial Hotel

10/10 Excellent

"Our stay was nice, king size bed was very comfortable and warm. Carpet in the rooms were well maintained, and bathrooms look new. Overall, a comfortable night!"

Windmill Motel Restaurant

10/10 Excellent

"It was just what I needed for my stay in the area…. Clean, comfortable and quiet. The staff were very helpful and friendly… I enjoyed my stay there. The price was right too!"

Hampton Inn & Suites Greenfield

8/10 Good

"l"

The Inn At Crumpin Fox

8/10 Good

"Very helpful staff"

More cheap stays in Winchester

The Putney Inn

57 Putney Landing Rd Putney VT

Rp1.506.537

Rp1.657.102 total

25 Oct - 26 Oct

includes taxes & fees

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

Rp1.612.881

Rp1.749.976 total

27 Oct - 28 Oct

includes taxes & fees

7/10 Good! (1,007 reviews)

Gardner Inn

22 Pearson Blvd Gardner MA

Rp1.772.397

Rp1.979.714 total

18 Oct - 19 Oct

includes taxes & fees

7.6/10 Good! (68 reviews)

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

Rp2.219.972

Rp2.408.670 total

27 Oct - 28 Oct

includes taxes & fees

Latchis Hotel

50 Main Street Brattleboro VT

Rp2.233.220

Rp2.456.542 total

28 Sept - 29 Sept

includes taxes & fees

8.6/10 Excellent! (989 reviews)

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT

Rp2.692.074

Rp2.961.280 total

25 Oct - 26 Oct

includes taxes & fees

Hotels in Winchester with star rating

Frequently asked questions

What's the best place to stay in Winchester?

The Colonial Hotel, located 26.3 mi (42.3 km) from the heart of Winchester, is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Colonial Motel and Latchis Hotel. See all available top hotels, or vacation rentals in Winchester.

If I need to cancel my hotel reservation in Winchester, will I receive a refund?

Yes, the majority of hotel reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your arrival date. If you have a non-refundable reservation, you may still be able to cancel and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

What are some hotels with pools in Winchester?

The Colonial Hotel: Features a sauna, an indoor pool and free self parking. Keene Elm City Hotel, an Ascend Collection Hotel and Best Western Plus Keene Hotel are a couple of other choices that offer an on-site pool. View all hotels with pools in Winchester.

What is staying in Winchester like?

Visitors to Winchester will definitely enjoy the lakeside setting. Tourists can also enjoy so much more including its forests. In Winchester, there are 6 hotels and other accommodation options to choose from. Find out more about Winchester.

What are the top places to visit in Winchester?

Natural beauty is on display at Birch Point, Cass Pond and Royalston State Forest. A couple of additional sights to add to your itinerary are Winchester Speedpark and New England Sweetwater Farm & Distillery. Take a look at what more there is to see and do in Expedia's Winchester guide.

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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Book Hotels in Winchester on Expedia.com

Find hotels in Winchester, NH from Rp1.240.679

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Winchester

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Winchester hotels

1. The Inn At Crumpin Fox

2. Windmill Motel Restaurant

3. Black Mountain Inn

4. Hampton Inn Brattleboro

5. The Covered Bridge Inn

6. Latchis Hotel

7. Colonial Motel

8. Comfort Inn & Suites Brattleboro I-91

9. The Carriage Barn Inn

10. Holiday Inn Express Hotel & Suites Brattleboro by IHG

11. Keene Elm City Hotel, an Ascend Collection Hotel

12. Days Inn by Wyndham Keene NH

13. Centennial House

14. Hampton Inn & Suites Greenfield

15. Vikings Villages Resort

16. The Putney Inn

17. Hampton Inn & Suites Keene

18. Best Western Plus Keene Hotel

19. Fairfield Inn & Suites by Marriott Keene Downtown

20. Riverside Hotel, an Ascend Collection Hotel

Stay near popular Winchester attractions

Winchester Speedpark

New England Sweetwater Farm & Distillery

Cass Pond

Richmond Wildlife Manangement Area

Barden State Wildlife Management Area

Loring Field

Bennett Gorge

Conant Public Library

Learn more about Winchester

Top Winchester Hotel Reviews

Best Western Plus Keene Hotel

Days Inn by Wyndham Keene NH

Gardner Inn

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Deerfield Inn

The Colonial Hotel

Windmill Motel Restaurant

Hampton Inn & Suites Greenfield

The Inn At Crumpin Fox

More cheap stays in Winchester

The Putney Inn

Days Inn by Wyndham Keene NH

Gardner Inn

Keene Elm City Hotel, an Ascend Collection Hotel

Latchis Hotel

Comfort Inn & Suites Brattleboro I-91

Hotels in Winchester with star rating

Frequently asked questions

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