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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 9 B&B in Windsor with updated reviews, rates, and availability.

Maple Hill Farm Inn
Outdoor banquet area

Maple Hill Farm Inn

3.0 star property
9.8 out of 10, Exceptional, (126)
"Beautiful B&B, the inn keepers are beyond friendly and helpful. "
The price is AED 654
AED 713 total
includes taxes & fees
4 May - 5 May
Maple Hill Farm Inn
Clary Lake Bed and Breakfast
View from property

Clary Lake Bed and Breakfast

3.0 star property
9.6 out of 10, Exceptional, (104)
"The perfect place to stay-friendly hosts, a lovely home and beautiful grounds. We thoroughly enjoyed our stay here and hope to return. "
The price is AED 441
AED 480 total
includes taxes & fees
3 May - 4 May
Clary Lake Bed and Breakfast
Pressey House Lakeside Bed & Breakfast
Exterior

Pressey House Lakeside Bed & Breakfast

3.0 star property
The price is AED 890
AED 970 total
includes taxes & fees
1 Jun - 2 Jun
Pressey House Lakeside Bed & Breakfast
Blueberry Fields B&B
Front of property

Blueberry Fields B&B

3.0 star property
10.0 out of 10, Exceptional, (91)
"Perfect place, perfect people, Excellent food, beautiful setting. "
The price is AED 731
AED 797 total
includes taxes & fees
5 May - 6 May
Blueberry Fields B&B
The Waldoboro Inn Room 3
Exterior

The Waldoboro Inn Room 3

The Waldoboro Inn Room 3
The Waldoboro Inn Room 5
Exterior

The Waldoboro Inn Room 5

8.0 out of 10, Very Good, (1)
"A very unique property out of a Steven King mystery. The bathroom had a wonderful handpainted mural. Couple of miner things, light over bathroom sink did not work and no tissues in room."
The price is AED 977
AED 1,213 total
includes taxes & fees
4 May - 5 May
The Waldoboro Inn Room 5
The Waldoboro Inn Room 1
Exterior

The Waldoboro Inn Room 1

The Waldoboro Inn Room 1
Newcastle Inn
Front of property

Newcastle Inn

3.5 star property
9.8 out of 10, Exceptional, (6)
"We enjoyed our stay at the Newcastle Inn. Our innkeeper, Julie, was friendly and helpful. She made an excellent recommendation for dinner and served a delicious breakfast of scrambled eggs and bacon. We had never spent time in the Newcastle area. We will definitely visit the Inn again. "
Newcastle Inn
Le Vatout
Exterior

Le Vatout

3.0 star property
8.0 out of 10, Very Good, (48)
"DO NOT BOOK THIS PLACE. iT IS A RIP-OFF. I GOT THErE EARLY AND HAD THE MISFORTUNE TO GET INSIDE THE PROPeRTY EARLY. THIS IS A HOARDER HOME THAT SMELLS LIKE CAT PEE. BOTH MY HUSBAND AND I WERE SCARED TO STAY ThERE. Also they suggest you have dinner there and the place is overgrown with plants. Truly in 44 years of traveling in the US and around the world this is the worst place to stay that I have ever been. We left and called Expedia to cancel even before the check in time and the owner...
Le Vatout
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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Other property types in Windsor

Downtown! Views! Dining! King & Queen beds!
Fridge, microwave, oven, stovetop

Downtown! Views! Dining! King & Queen beds!

2.0 star property
10.0 out of 10, Exceptional, (9)
"My daughter and I came to Maine for my birthday. The VRBO rental located on Water Street was flawless and exceeded our expectations. Beautifully appointed, Spotlessly clean, cozy and wonderful beds, bedding and pillows. Fun being right on the main street and walkable to most everything. The hosts were so accommodating, wish they had places all over the world. One recommendation is a tv on the kitchen level, I like tv. But the tv area upstairs is simply wonderful, so cozy. Views are delightful...
Downtown! Views! Dining! King & Queen beds!
April Special, Lake Great Pond, Dog Friendly
Outdoor dining

April Special, Lake Great Pond, Dog Friendly

10.0 out of 10, Exceptional, (36)
"Really enjoyed our stay, will come back. "
The price is AED 575
AED 1,175 total
includes taxes & fees
5 May - 6 May
April Special, Lake Great Pond, Dog Friendly
Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop
Fridge, microwave, oven, stovetop

Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop

Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop
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.

Frequently asked questions

Searching for B&Bs in Windsor?
Whether you’re on a family vacation and want a small, cozy place to stay, or you’re a solo traveler hoping to get some tips from locals, a B&B might be the right choice for your trip.
Why should you consider a B&B over a traditional hotel room?
Every B&B has its own unique feel. Whether it’s a garden for guests to admire or a beautiful breakfast room, the tiny details are what make bed and breakfasts the perfect escape.
What are the best bed and breakfasts in Windsor?
Here are some well-liked B&Bs in the surrounding area: Maple Hill Farm Inn: 8 rooms. 12.8 mi (20.6 km) from the heart of Windsor. Enjoy the free cooked breakfast and private yard. Pressey House Lakeside Bed & Breakfast: 5 rooms. 17.4 mi (28.1 km) from the downtown core. Enjoy the deli and bar/lounge. Blueberry Fields B&B: 5 rooms. Situated 7.7 mi (12.4 km) from the heart of Windsor. Enjoy the free full breakfast and massage services. Clary Lake Bed and Breakfast: 3 rooms. 7.4 mi (11.8 km) from the heart of downtown. Enjoy the soaking bathtubs and fireplace in the lobby. The Waldoboro Inn Room 5: Located 18 mi (28.9 km) from the core of Windsor.
When should I stay at a B&B in Windsor?
When you’re planning your escape to Windsor, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Windsor are January, December, March, and February, with each month seeing an average of 10 inches of snowfall.
What is there to do in Windsor?
When you want to spend some time in the great outdoors, Capitol Park and Damariscotta Lake are some notable spots. You might put St George Lake and Kennebec River on your list if you want to see more of the area.
How can I get to and around Windsor?
Mapping out your trip in and around Windsor is easy with these transportation options. Fly into Augusta, ME (AUG-Augusta State), which is located 10.5 mi (16.9 km) from the heart of the city. Otherwise, look for flights into Waterville, ME (WVL-Robert Lafleur), which is 16.2 mi (26 km) away. If you’d like to venture out around the area, you may want a rental car for your journey.