A welcome sign at Cradle of Hockey, Long Pond, Windsor, Nova Scotia.

Find Romantic Hotels in Windsor

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Windsor Romantic Hotels

Tonight
Sep 29 - Sep 30
Tomorrow
Sep 30 - Oct 1
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Windsor romantic hotels

A building labeled 'The August House' with outdoor seating and string lights.
A two-story house with a sign reading "The August House."
A neatly made bed with white linens and striped pillows, a framed landscape painting above it, and a dark headboard.
A living room with a fireplace, a chandelier, and teal walls.

1. The August House

The August House
Windsor
United States
Charles
￥21,603
￥25,798 total
includes taxes & fees
Oct 19 - Oct 20
The August House
A large house with a spacious driveway, a well-maintained garden, and a vineyard in the background.
A dining area with tables set for a meal, featuring wine glasses and orange napkins.
A view through a wooden-framed window with multiple panes, overlooking a garden with pink flowers and green grass.
A living room with a blue sofa, two red armchairs, a glass coffee table, and a TV on a white stand.

2. The Inn at Grand Pre Winery

The Inn at Grand Pre Winery
Grand Pre
Canada
Milena
￥37,368
￥42,600 total
includes taxes & fees
Oct 22 - Oct 23
The Inn at Grand Pre Winery
An outdoor patio with wooden pergola, seating, and a view of the landscape.
A modern house with a stone retaining wall, a well-maintained garden, and a clear sky.
A hotel room with two beds, a large window with a view of the garden, and a wooden ceiling.
A modern building with a covered outdoor area, a well-maintained lawn, and a distant view of a landscape with trees and hills.

3. Old Orchard Inn

Old Orchard Inn
Wolfville Ridge
Canada
Michael
￥23,394
￥27,935 total
includes taxes & fees
Oct 4 - Oct 5
Old Orchard Inn
A covered outdoor seating area with chairs and tables, a stone pillar, and a view of a building with large windows.
A wooden door with stained glass windows, a chandelier, and a floral carpet.
A dining table set with a white plate, a teapot, and a rose.
A hotel room with two beds, each with a wooden headboard, white bedding, and a grey throw blanket. There are wall-mounted lamps and framed pictures above the beds.

4. Tattingstone Inn

Tattingstone Inn
Wolfville
Canada
Loreen
￥27,327
￥31,152 total
includes taxes & fees
Oct 25 - Oct 26
Tattingstone Inn
A bedroom with a large bed, white pillows, and a view of a body of water through a sliding glass door.
A two-story building with a sign reading "AVEDA" on the ground floor.
A reception area with a framed photo, a small table with magazines, a fireplace, and a wooden accent wall.
A hotel room with a bed, a desk, a chair, a TV, a microwave, and a refrigerator.

5. Micro Boutique Living Wolfville

Micro Boutique Living Wolfville
Wolfville
Canada
Kelly
￥20,987
￥23,925 total
includes taxes & fees
Oct 18 - Oct 19
Micro Boutique Living Wolfville
A hotel reception area with a wooden reception desk, a gold cart, and a large window with a view of the lobby.
A modern restaurant with a central dining area, a counter with a beverage dispenser, and a kitchen in the background.
A modern lobby with a marble wall, a flat-screen TV, and two sofas.
A reception area with a counter, a computer monitor, a blue chair, and a vase with flowers.

6. Slumber Inn

Slumber Inn
New Minas
Canada
Elaine
￥19,919
￥23,390 total
includes taxes & fees
Oct 4 - Oct 5
Slumber Inn
A bedroom with a large bed, a TV mounted on the wall, a window with a view, and a seating area with two chairs and a small table.
A compact kitchen with white cabinetry, a black countertop, a small island with a sink, and a coffee maker.
A small, white-walled room with a white table, two potted plants, a candle, and a microwave.
A compact kitchen with white cabinetry, a microwave, a coffee maker, and a small table with a tray.

7. Studio-like Comfort in Wolfville’s Beating Heart

Studio-like Comfort in Wolfville’s Beating Heart
Wolfville
Canada
David
￥15,768
￥32,280 total
includes taxes & fees
Oct 27 - Oct 28
Studio-like Comfort in Wolfville’s Beating Heart
A cabin with a porch, outdoor seating, and string lights.
A wooden cabin with a large open door, a small table, and a hanging light fixture.
A rustic cabin interior with a kitchenette, a dining table, and a leather rug.
A wooden cabin with a balcony, a painting of a landscape on the side, and a set of stairs leading to the entrance.

8. Pet-Friendly Cabin | Sleeps 2 | Private Fire Pit

Pet-Friendly Cabin | Sleeps 2 | Private Fire Pit
Mount Uniacke
United States
Charie
￥11,543
￥20,690 total
includes taxes & fees
Oct 6 - Oct 7
Pet-Friendly Cabin | Sleeps 2 | Private Fire Pit
A modern kitchen with a large island, pendant lights, and a view to the outside.
A modern living room with a sofa, coffee table, and a dining area with chairs. There is a kitchen area with a sink and a shower.
A modern bedroom with a large window, a bed with pillows, a chair, and a desk.
A laundry room with a washing machine and dryer, a shower with a glass door, and a hallway leading to a dining area.

9. Suite 201 - Spacious One Bedroom Apartment-Style Suite in Hybrid Hotel Wolfville

Suite 201 - Spacious One Bedroom Apartment-Style Suite in Hybrid Hotel Wolfville
Wolfville
United States
Harry G.
￥27,538
￥43,625 total
includes taxes & fees
Oct 21 - Oct 22
Suite 201 - Spacious One Bedroom Apartment-Style Suite in Hybrid Hotel Wolfville
A large, multi-story house with a prominent balcony, a garage, and a driveway.
A two-story house with a covered porch, outdoor seating, and a garden.
A hotel room with a bed, two chairs, a desk, a television, and a red table with a folder.
A sign for Gingerbread House Inn with a bed & breakfast symbol.

10. L`Acadie Room - Kitchenette, Patio, DT

L`Acadie Room - Kitchenette, Patio, DT
Wolfville
Canada
Anneke
￥19,068
￥25,282 total
includes taxes & fees
Oct 12 - Oct 13
L`Acadie Room - Kitchenette, Patio, DT
View all properties

Top Windsor Hotel Reviews

Frequently asked questions

Searching for romantic hotels in Windsor?
Are you and your partner looking for a romantic vacation? If you want to explore the area, you might head to West Hants Historical Society, Trecothic Creek and Windsor Railway, or Haliburton House Museum. If you're interested in staying near a certain attraction, you can sort properties by neighborhood or distance to top landmarks, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Windsor?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Windsor: The hottest months are usually August and July with an average temp of 62°F, while the coldest months are February and January with an average of 31°F. The snowiest months in Windsor are February, January, December, and November, with each month seeing an average of 17 inches of snowfall.
What is there to do in Windsor?
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 Windsor. If you want to spend a day exploring, you might consider a stop at West Hants Historical Society, Trecothic Creek and Windsor Railway, or Haliburton House Museum.
What's the best way to get to Windsor and around town during my romantic getaway?
This information about transportation options in Windsor might help your romantic trip go off without a hitch: To get to Windsor, you can fly into Stanfield Intl. Airport (YHZ), which is the closest major airport, located 30.9 mi (49.8 km) from the city center. If you'd like to venture out around the area, you may want to rent a car for your trip.

Explore a world of travel with Expedia