Windsor Holiday Rentals, Hillsboro: Private House Rentals

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Our top choices for Windsor hotels

A modern bedroom with two beds, a wooden headboard, a small table, and a hanging light fixture.

A motel sign with '467 Newport' and 'Motel' written on it, and a 'VAGANZY' label.

A modern bathroom with a toilet, sink, and towel rack.

A motel with a grassy lawn, a parking lot, and a row of trees in the background.

1. Newport Motel

Newport

Andrew

2.778.002 ₫

3.014.132 ₫ total

includes taxes & fees

10 Sept - 11 Sept

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

A hotel room with a large bed, two smaller beds, a desk with a TV, a chair, and a view of the outdoors.

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

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

2. Best Western Plus Keene Hotel

Keene

Julia

3.872.957 ₫

4.202.288 ₫ total

includes taxes & fees

10 Sept - 11 Sept

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

A living room with a brick wall, two armchairs, a sofa, a coffee table, and a patterned rug.

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

3. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

James

5.284.377 ₫

5.733.549 ₫ total

includes taxes & fees

17 Sept - 18 Sept

A wooden picnic table with a bottle and two glasses, surrounded by lush greenery and a wooden fence.

A modern bedroom with a large bed, a nightstand, a lamp, and a stone pillar.

A room with a wooden coffee table, two chairs, a bookshelf, and a large mirror on the wall.

A hotel with a snow-covered driveway, Christmas lights, and a large tree in front.

4. Riverhouse by Weekender (Formerly Jack Daniels Inn)

Peterborough

James

3.797.266 ₫

4.401.798 ₫ total

includes taxes & fees

7 Oct - 8 Oct

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

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.

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

5. Days Inn by Wyndham Keene NH

Keene

Alex

2.717.568 ₫

2.948.561 ₫ total

includes taxes & fees

14 Sept - 15 Sept

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

A hotel room with two beds, a desk, an orange chair, and a view of buildings through the window.

An indoor swimming pool with clear water, a glass railing, and a seating area with tables and chairs.

A multi-story brick building with a sign reading "COURTYARD BY MARRIOTT".

6. Courtyard by Marriott Keene Downtown

Keene

Deborah

5.172.607 ₫

5.612.279 ₫ total

includes taxes & fees

10 Sept - 11 Sept

A historic brick building with a porch and a sign reading "Burrell House."

A covered outdoor seating area with tables and chairs, overlooking a residential street with houses and a road.

A bedroom with a large bed, a wooden desk, and three chairs. There are three windows with shutters.

A kitchen with a microwave, coffee maker, and a KUPPST refrigerator. There are two stools and a small shelf with a vase.

7. The Burrell House

Keene

Justin

3.028.232 ₫

3.376.479 ₫ total

includes taxes & fees

10 Sept - 11 Sept

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.

An indoor swimming pool with lounge chairs and a sign indicating no lifeguard on duty and no diving.

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

8. Hampton Inn & Suites Keene

Keene

sheri

4.134.966 ₫

4.486.438 ₫ total

includes taxes & fees

17 Sept - 18 Sept

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

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.

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

A bench in front of an apple tree with ripe apples.

9. The Carriage Barn Inn

Keene

Jonathan

4.092.754 ₫

4.440.638 ₫ total

includes taxes & fees

28 Sept - 29 Sept

A sign for the Henniker Motel with a mountain and sun graphic.

A house with a large lawn and a rainbow in the sky.

An indoor swimming pool with a tiled edge, wooden paneling, and a door leading to another room.

A room with two armchairs, a small table with a lamp, and a window with a view of trees.

10. Henniker Motel

Henniker

glen

3.872.957 ₫

4.202.288 ₫ total

includes taxes & fees

10 Sept - 11 Sept

A wooden cabinet with glass doors, a mirror, and a vase with flowers.

A dining table with chairs, a menu, and a plate of pastries.

A cozy living room with a fireplace, a red armchair, and a person holding a drink.

11. Colby Hill Inn

Henniker

Taisha

5.766.781 ₫

6.256.958 ₫ total

includes taxes & fees

10 Sept - 11 Sept

A stone-clad building entrance with a covered patio and benches.

A hotel entrance with a stone facade, a covered entrance area, and a sign reading "Mountain Edge."

An indoor swimming pool with wooden walls and ceiling, clear water, and multiple lanes.

A spacious lobby with a high ceiling, a stone wall, a wooden staircase, and a buffet table.

12. Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

Newbury

Leah

3.906.748 ₫

4.661.988 ₫ total

includes taxes & fees

22 Sept - 23 Sept

A restaurant with wooden tables and chairs, arranged in a row, with large windows on one side.

A hand holding a wine glass at a bar with a row of wine bottles in the background.

A covered outdoor seating area with tables and chairs, a person in an apron, and various beverages on the table.

A building with an entrance sign, large windows, and outdoor plants.

13. The New London Inn

New London

Sarah

3.719.598 ₫

4.035.673 ₫ total

includes taxes & fees

16 Sept - 17 Sept

A hotel room with two beds, a canopy bed, a wooden headboard, a chair, a window, and a wall-mounted sign.

A cozy living room with a stone fireplace, wooden benches, a leather sofa, and a bookshelf filled with books and decorative items.

A poolside area with a wooden ceiling, a seating arrangement with chairs and cushions, and skis and snowboards on the wall.

Two vending machines labeled 'Hideaway' with snacks and drinks inside.

14. Hideaway Inn Mt.Sunapee

Newbury

Lenny

3.056.777 ₫

3.316.603 ₫ total

includes taxes & fees

1 Oct - 2 Oct

A two-story building with a white facade and green shutters, a covered front porch, and a sign for the "M" Inn.

A dining area with two tables, chairs, and a radiator.

A staircase with a patterned carpet, a wooden table with a lamp, and a wall with floral wallpaper.

A porch with a wooden bench and a bench with cushions.

15. Monadnock Inn

Jaffrey

Jed

4.389.178 ₫

4.762.178 ₫ total

includes taxes & fees

13 Sept - 14 Sept

A traditional two-story house with a porch and a large tree in front.

A dining area with a table set for four, a painting on the wall, and a statue on a pedestal.

A cozy room with wooden walls, a large armchair, a smaller chair, a table, and a wood-burning stove.

A wooden dock leading to a stone staircase with a view of a white house and green chairs by a lake.

16. Follansbee Inn

North Sutton

David

4.968.822 ₫

5.391.208 ₫ total

includes taxes & fees

16 Sept - 17 Sept

A large estate with multiple buildings, a swimming pool, and a well-maintained lawn.

A neutral-toned armchair and a small wooden table with a glass top, positioned in a bright room with white walls and a window.

A spacious dining area with a fireplace, wooden tables, and chairs.

A reception desk with a wooden top labeled "Blue Bear Inn on Crooked Mountain," a display of hats, and a mannequin wearing a cap.

17. Blue Bear Inn

Francestown

Joel

5.883.775 ₫

6.383.880 ₫ total

includes taxes & fees

15 Sept - 16 Sept

A bar area with a cake on a glass stand, plates, a pink napkin, and a rolled dessert on a plate.

A historic building with a prominent corner turret and a wrap-around porch.

A residential area with a white house, a white bridge, and a gazebo.

A room with a wooden floor, a wooden chair, a table, a mirror, and a red candle on a table.

18. Rosewood Country Inn

Bradford

Monica

5.828.930 ₫

6.324.357 ₫ total

includes taxes & fees

10 Sept - 11 Sept

A wooden bar area with a countertop, glasses, and a chalkboard menu.

A rustic dining area with wooden tables and chairs, a fireplace, and a clock on the wall.

A bar area with wooden cabinets, a counter, and a notice sign.

A cozy room with a stone fireplace, wooden furniture, and a table with chairs.

19. Brook Road Inn

Goshen

"Gave me a little sore throat and mild congestion because of the dust in the atmosphere of my bedroom but overall clean and neat environment. When stepping out of the room the smell of the furniture was be noticed as being a bit antique on the cheaper rooms. But regardless of that, everything was absolutely beautiful thank you! I liked longing on the couch down the stairs even took a nap. Really nice view outside and environment to be in."

Jennifer

1.731.134 ₫

2.780.757 ₫ total

includes taxes & fees

10 Sept - 11 Sept

A modern living room with a sectional sofa, a wooden coffee table, and a large window with blinds.

A wooden deck with a table and chairs, surrounded by greenery and a wooden fence.

A large brick building with a prominent tower, surrounded by trees and a hilly landscape.

A dining area with a wooden table and chairs, two windows with a view of trees, a refrigerator, and a water dispenser.

20. Brook Road Cabin

Goshen

Jill

4.460.630 ₫

7.434.405 ₫ total

includes taxes & fees

10 Sept - 11 Sept

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Stay near popular Windsor attractions

Black Pond

Commune with nature and explore the great outdoors at Black Pond during your travels in Windsor.

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Windsor Town Hall

Windsor Town Hall is just one of the places to see in Windsor, so why not enjoy the other things to explore during your travels?

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Top Windsor Hotel Reviews

Hampton Inn & Suites Keene

10/10 Excellent

"It was clean and very comfy"

The Burrell House

10/10 Excellent

"Wonderful inn in the heart of Keene. Easy walk to everything. I have stayed there numerous times."

Hideaway Inn Mt.Sunapee

8/10 Good

"This is a good basic place to stay- there isn't many frills. It provides a nice bed and bathroom. Good for a stay when you just need the essentials. Location for Mt Sunapee is excellent."

Blue Bear Inn

10/10 Excellent

"Absolutely amazing Inn!! You’re really missing out if you don’t stay here! To many positives to list them all."

Monadnock Inn

10/10 Excellent

"Very nice, clean, and a good vibe. An older building but very charming. Would certainly stay again."

Colby Hill Inn

8/10 Good

"The inn was pretty and the staff was very nice. The breakfast was delicious and plentiful. Our room was comfortable but all the pictures shown are not quite what it looks like at this time."

Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

8/10 Good

"First, the service was amazing. The afternoon/evening front desk gentlemen was extremely kind and helpful as we navigated an issue with the room we were originally given (that turned out to not be an issue so won’t bother mentioning). The rooms were slightly dated but clean and well maintained. The only downside of the room was the carpet - it wasn’t awful but was old and a bit musty. We are very sensitive to smells and allergens so others may not notice. That said it didn’t affect our allergies too much so it wasn’t that bad. Room comes with basic cooking equipment, plates and silverware. The room we got was a two bedroom but the queen bedroom doesn’t have a door that closes - it’s a separate room but is open to the living room/kitchen. This wasn’t an issue for us but worth noting for others. Beds were clean and looked new but weren’t the nicest mattresses. Same with the pillows. We did go to the indoor pools - it was pretty well maintained. They had locker rooms and a dry sauna but we didn’t use either. Continental breakfast was as you’d expect. Nothing hot was served but lots of options - including a whole gluten free section which you NEVER see at hotels and I great appreciated. The hotel was nice and the staff great but it definitely had “we were a reeeallly nice hotel before the pandemic and then we lost a lot of our extras” vibes. They used to have a spa, a bar, an outdoor pool and a restaurant but those are all gone. It was fine as is though."

Fairfield Inn & Suites by Marriott Keene Downtown

10/10 Excellent

"Right in the middle of town. Very comfortable. Nice breakfast in the morning. Liked the candy in the lobby."

Brook Road Inn

8/10 Good

More cheap stays in Windsor

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

2.717.568 ₫

2.948.561 ₫ total

14 Sept - 15 Sept

includes taxes & fees

7/10 Good! (1,008 reviews)

Newport Motel

467 Sunapee St Newport NH

2.778.002 ₫

3.014.132 ₫ total

10 Sept - 11 Sept

includes taxes & fees

Hideaway Inn Mt.Sunapee

1403 New Hampshire Rte 103 Newbury NH

3.056.777 ₫

3.316.603 ₫ total

1 Oct - 2 Oct

includes taxes & fees

8.4/10 Very good! (262 reviews)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

80 Concord Street Peterborough NH

3.797.266 ₫

4.401.798 ₫ total

7 Oct - 8 Oct

includes taxes & fees

Hampton Inn & Suites Keene

126 Key Rd Keene NH

4.134.966 ₫

4.486.438 ₫ total

17 Sept - 18 Sept

includes taxes & fees

8.8/10 Excellent! (409 reviews)

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

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Frequently asked questions

What's the seasonal weather like in Windsor?

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 -3°C. The snowiest months in Windsor are January, March, February and November, with each month seeing an average of 19 cm of snowfall.

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Car hire near Hillsborough County

Book Hotels in Windsor on Expedia.com

Find hotels in Windsor, NH from 2.780.757 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Windsor

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Windsor hotels

1. Newport Motel

2. Best Western Plus Keene Hotel

3. Fairfield Inn & Suites by Marriott Keene Downtown

4. Riverhouse by Weekender (Formerly Jack Daniels Inn)

5. Days Inn by Wyndham Keene NH

6. Courtyard by Marriott Keene Downtown

7. The Burrell House

8. Hampton Inn & Suites Keene

9. The Carriage Barn Inn

10. Henniker Motel

11. Colby Hill Inn

12. Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

13. The New London Inn

14. Hideaway Inn Mt.Sunapee

15. Monadnock Inn

16. Follansbee Inn

17. Blue Bear Inn

18. Rosewood Country Inn

19. Brook Road Inn

20. Brook Road Cabin

Stay near popular Windsor attractions

Black Pond

Windsor Town Hall

Top Windsor Hotel Reviews

Hampton Inn & Suites Keene

The Burrell House

Hideaway Inn Mt.Sunapee

Blue Bear Inn

Monadnock Inn

Colby Hill Inn

Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

Fairfield Inn & Suites by Marriott Keene Downtown

Brook Road Inn

More cheap stays in Windsor

Days Inn by Wyndham Keene NH

Newport Motel

Hideaway Inn Mt.Sunapee

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Hampton Inn & Suites Keene

Keene Elm City Hotel, an Ascend Collection Hotel

Frequently asked questions

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