Search Romantic Hotels in Winchester

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Check availability on Winchester Romantic Hotels

Tonight
30 Nov - 1 Dec
Tomorrow
1 Dec - 2 Dec
Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec

Top Winchester Romantic Hotels

Reception
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

3.0 star property
Keene
8.8 out of 10, Excellent, (1007)
"Lovely hotel"
United States
ronald
The price is 4.235.537 ₫
4.595.557 ₫ total
includes taxes & fees
5 Dec - 6 Dec
Courtyard by Marriott Keene Downtown
Hiking
Latchis Hotel

Latchis Hotel

2.5 star property
Brattleboro
8.4 out of 10, Very good, (833)
"Great stay"
United States
Jason
The price is 3.440.632 ₫
3.784.695 ₫ total
includes taxes & fees
1 Dec - 2 Dec
Latchis Hotel
Free daily full breakfast
Centennial House

Centennial House

3.5 star property
Northfield
9.6 out of 10, Exceptional, (173)
"The house was cozy and inviting. Felt the history all around me and the breakfast made and served by Joan was great. We recommend this place for those looking for that historical b&b experience. "
United States
Paul
The price is 5.309.252 ₫
5.611.879 ₫ total
includes taxes & fees
26 Dec - 27 Dec
Centennial House
Sun deck
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (628)
"Clean room, beautiful location"
United States
Marcie
The price is 4.011.435 ₫
4.352.407 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Riverside Hotel, an Ascend Collection Hotel
Front of property
Colonel Williams Inn

Colonel Williams Inn

3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (340)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
United States
scott
The price is 4.152.488 ₫
4.567.736 ₫ total
includes taxes & fees
1 Dec - 2 Dec
Colonel Williams Inn
Exterior
Monadnock Inn

Monadnock Inn

2.5 star property
Jaffrey
7.6 out of 10, Good, (276)
"It is a Beautiful Old Charm Inn. Everything was great. I would definitely come back and stay there again. "
United States
Sharon-Ann C
Monadnock Inn
Lobby
Chesterfield Inn

Chesterfield Inn

4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104)
"Great stay"
United States
Wayne
The price is 7.939.556 ₫
8.614.500 ₫ total
includes taxes & fees
1 Dec - 2 Dec
Chesterfield Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchester Hotel Reviews

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Frequently asked questions

Searching for romantic hotels in Winchester?
If you and your partner need a romantic escape, we'd like to help you plan for it. Our guests also enjoy Winchester for its lakeside setting. You might consider checking out some of the nearby sights and attractions such as Birch Point, Pisgah State Park or New England Sweetwater Farm & Distillery. If you're interested in staying close to a certain attraction, you can sort by neighbourhood and proximity to top sights, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Winchester?
If you're hoping to get lost in the rain on your romantic getaway, take a look at these details about year-round temperatures 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.
What is there to do in Winchester?
There's nothing better than experiencing a new place with your sweetheart, so consider taking time to discover all there is to see and do in Winchester. Couples looking to get out in nature will enjoy Winchester for its lakeside setting. You might think about stopping by Birch Point, Pisgah State Park or New England Sweetwater Farm & Distillery while you're seeing the sights.