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Check prices for these dates

Next weekend
11 Rab. II - 13 Rab. II
In two weeks
18 Rab. II - 20 Rab. II
In one month
2 Jum. I - 4 Jum. I
In two months
30 Jum. I - 1 Jum. II

Compare 23 B&B in Winchester with updated reviews, rates, and availability.

The Revolution Hotel
Deluxe Room, 2 Double Beds (Bath in Room) | Premium bedding, down comforters, pillowtop beds, in-room safe

The Revolution Hotel

3.5 star property
8.8 out of 10, Excellent, (1993)
"Great discovery! Such a unique and quirky hotel experience with surprising luxury. Wonderful staff!"
The price is SAR 672
SAR 782 total
includes taxes & fees
8 Apr - 9 Apr
The Revolution Hotel
Harborside Inn Of Boston
Front of property

Harborside Inn Of Boston

4.0 star property
9.2 out of 10, Wonderful, (5003)
"Great location near Quincy market. Walkable. Affordable. The design of the room was to really cute and the bed was comfortable. Was not offered the VIP wine that was advertised for booking thru hotels. Com. Fast check in. Only real complaint is that the heater made the room really dry and I woke up with a bad headache"
The price is SAR 784
SAR 913 total
includes taxes & fees
13 Apr - 14 Apr
Harborside Inn Of Boston
citizenM Boston Back Bay
Exterior

citizenM Boston Back Bay

4.0 star property
9.4 out of 10, Exceptional, (952)
"CitizenM never disappoints "
The price is SAR 653
SAR 760 total
includes taxes & fees
13 Apr - 14 Apr
citizenM Boston Back Bay
Omni Boston Hotel at the Seaport
View from room

Omni Boston Hotel at the Seaport

4.0 star property
9.2 out of 10, Wonderful, (3366)
"Property was great. Staff are great. Room immaculate. Unfortunately there was 2 conventions when there so it was hard for a solo traveller to avail of the property amenites as it was over run. Has to go out to eat each night which was unfortunate."
The price is SAR 789
SAR 1,049 total
includes taxes & fees
4 May - 5 May
Omni Boston Hotel at the Seaport
The Godfrey Hotel Boston
Peruvian cuisine

The Godfrey Hotel Boston

4.0 star property
9.4 out of 10, Exceptional, (3880)
"The propert looks and feels good - staff are friendly, responsive & attentive. The decor is lovely. And the location is fantastic. Very pleased & would definitely stay here again."
The price is SAR 740
SAR 1,036 total
includes taxes & fees
10 Apr - 11 Apr
The Godfrey Hotel Boston
citizenM Boston North Station
Interior

citizenM Boston North Station

4.0 star property
9.2 out of 10, Wonderful, (3284)
"My son and I absolutely loved our stay at this hotel! It is the perfect location for catching a game at TD Garden, and overall location is great for getting around the city. We walked everywhere except Fenway Park but that was a fun ride in the T we wanted to experience anyway. Staff was awesome, room was clean, and we got the city view room - that was my favorite part, the view was GORGEOUS. I’ll never stay anywhere else in Boston, this is THE hotel. "
The price is SAR 634
SAR 739 total
includes taxes & fees
27 Apr - 28 Apr
citizenM Boston North Station
The Dagny Boston
Interior detail

The Dagny Boston

4.0 star property
9.4 out of 10, Exceptional, (5660)
"Exceptional staff great property. Perfect location "
The price is SAR 747
SAR 1,001 total
includes taxes & fees
13 Apr - 14 Apr
The Dagny Boston
Copley Square Hotel, a FOUND Hotel
Front of property

Copley Square Hotel, a FOUND Hotel

4.0 star property
8.6 out of 10, Excellent, (3561)
"The staff is excellently courteous and acomodating. I would start her again. Room the king was clean and spacious. There’s a microwave and coffee and vending machines. I got complementary water bottles which came in handy. Overall the staff was great and hotel was in the middle of everything. "
The price is SAR 578
SAR 673 total
includes taxes & fees
13 Apr - 14 Apr
Copley Square Hotel, a FOUND Hotel
Seaport Hotel Boston
Exterior

Seaport Hotel Boston

4.0 star property
9.6 out of 10, Exceptional, (2883)
"Beautiful hotel and surrounding area! "
The price is SAR 1,066
SAR 1,260 total
includes taxes & fees
4 May - 5 May
Seaport Hotel Boston
Encore Boston Harbor
Apartment, 2 Bedrooms | Premium bedding, down comforters, pillowtop beds, minibar

Encore Boston Harbor

5.0 star property
9.6 out of 10, Exceptional, (2866)
"very comfortable, clean and spacious rooms. Alexa assisted room options."
The price is SAR 1,048
SAR 1,171 total
includes taxes & fees
27 Apr - 28 Apr
Encore Boston Harbor
The Westin Boston Seaport District
Restaurant

The Westin Boston Seaport District

4.0 star property
9.0 out of 10, Wonderful, (1819)
"We will definitely stay here again!"
The price is SAR 638
SAR 874 total
includes taxes & fees
13 Apr - 14 Apr
The Westin Boston Seaport District
Hyatt Place Boston/Seaport District
Bar (on property)

Hyatt Place Boston/Seaport District

3.0 star property
9.4 out of 10, Exceptional, (1979)
"Staff was super helpful. They found me a room at 10 AM!"
The price is SAR 859
SAR 1,001 total
includes taxes & fees
13 Apr - 14 Apr
Hyatt Place Boston/Seaport District
Four Points by Sheraton Boston Newton
Room, 2 Queen Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

Four Points by Sheraton Boston Newton

3.5 star property
8.4 out of 10, Very Good, (2752)
"Convenient price"
The price is SAR 477
SAR 532 total
includes taxes & fees
27 Apr - 28 Apr
Four Points by Sheraton Boston Newton
Hilton Boston Park Plaza
Exterior

Hilton Boston Park Plaza

4.0 star property
8.4 out of 10, Very Good, (3364)
"Staff was responsive and helpful."
The price is SAR 667
SAR 929 total
includes taxes & fees
14 Apr - 15 Apr
Hilton Boston Park Plaza
Hampton Inn & Suites Boston Crosstown Center
Reception

Hampton Inn & Suites Boston Crosstown Center

3.0 star property
7.8 out of 10, Good, (1085)
"The T was much further away than I was led to expect and no one suggested the bus options that I did not find out about until my last day."
The price is SAR 525
SAR 612 total
includes taxes & fees
13 Apr - 14 Apr
Hampton Inn & Suites Boston Crosstown Center
The Colonnade Hotel Back Bay
Seasonal outdoor pool, cabanas (surcharge), pool umbrellas

The Colonnade Hotel Back Bay

4.0 star property
9.0 out of 10, Wonderful, (1739)
"Always my to go place to stay"
The price is SAR 1,059
SAR 1,365 total
includes taxes & fees
22 Apr - 23 Apr
The Colonnade Hotel Back Bay
La Quinta Inn & Suites by Wyndham Boston Somerville
Exterior

La Quinta Inn & Suites by Wyndham Boston Somerville

3.0 star property
7.6 out of 10, Good, (2574)
"Lovely morning breakfast very congenial "
The price is SAR 503
SAR 562 total
includes taxes & fees
27 Apr - 28 Apr
La Quinta Inn & Suites by Wyndham Boston Somerville
Hyatt Regency Boston
Miscellaneous

Hyatt Regency Boston

4.0 star property
9.0 out of 10, Wonderful, (1411)
"Not too far from bus station and going to shows at the Opera House!"
The price is SAR 638
SAR 874 total
includes taxes & fees
13 Apr - 14 Apr
Hyatt Regency Boston
Boston Marriott Copley Place
Pillowtop beds, in-room safe, desk, iron/ironing board

Boston Marriott Copley Place

4.0 star property
9.0 out of 10, Wonderful, (1510)
"No hot tub- pool was cold."
The price is SAR 987
SAR 1,281 total
includes taxes & fees
12 Apr - 13 Apr
Boston Marriott Copley Place
Hyatt Regency Boston/Cambridge
Exterior

Hyatt Regency Boston/Cambridge

4.0 star property
9.0 out of 10, Wonderful, (1755)
"Nice bar area."
The price is SAR 717
SAR 918 total
includes taxes & fees
23 Apr - 24 Apr
Hyatt Regency Boston/Cambridge
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 Winchester

Sonder 907 Main
Interior

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (452)
"Beautiful! What an incredible stay. Completely loved it."
The price is SAR 623
SAR 723 total
includes taxes & fees
13 Apr - 14 Apr
Sonder 907 Main
Maverick Suites at 28 Fenway
Deluxe Studio Suite (2nd Floor - Unit 202) | Living area | 50-inch Smart TV with satellite channels, Netflix, Hulu

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (177)
"Amazing stay, thank you!"
The price is SAR 383
SAR 807 total
includes taxes & fees
13 Apr - 14 Apr
Maverick Suites at 28 Fenway
Temple Place Suites
Deluxe Studio | Desk, iron/ironing board, free WiFi, bed sheets

Temple Place Suites

2.5 star property
6.8 out of 10, (194)
"The bed is super comfortable, self check in instructions are clear. Microwave, fridge, hairdryer and coffee maker all work excellently. The only downside is the shower hot water takes forever to start, and the heater is very noisy. It’s also close to the road, so the noises from the construction and roads are very noisy. Love the fact there’s elevator. "
The price is SAR 446
SAR 719 total
includes taxes & fees
24 Apr - 25 Apr
Temple Place Suites
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 Winchester?
If you want to find a place to stay with a small number of rooms and an intimate environment, a B&B might be just the right fit for your getaway to Winchester. If your ideal vacation to Winchester includes spending lots of time outside, Middlesex Fells Reservation is a good spot to enjoy the scenery.
How do you know if a B&B is the right choice for your stay?
B&Bs all have a unique charm. Whether it’s a picturesque garden or a beautiful dining room, the tiny details are what make bed and breakfasts the perfect escape.
What are the best B&Bs in Winchester?
Here are some well-liked B&Bs in the surrounding area: The Salem Inn: 13 mi (21 km) from the heart of Winchester. Enjoy the free cooked breakfast and unique décor. HomeStay - B&B - Near South Boston - JFK-Umass Area: 4 rooms. 10.2 mi (16.3 km) from the downtown core. Homestay BnB Near Downtown Boston: 5 rooms. Situated 9.7 mi (15.7 km) from the heart of Winchester. Irving House At Harvard: 5.5 mi (8.8 km) from the heart of downtown. Enjoy the local cuisine breakfast and deli. The College Club of Boston: 12 rooms. Located 7.6 mi (12.2 km) from the core of Winchester. Enjoy the library and coffee shop.
When should I stay at a B&B in Winchester?
When you’re planning your getaway to Winchester, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 33°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 5 inches of snowfall.
What is there to do in Winchester?
When you want to spend some time in the great outdoors, Middlesex Fells Reservation and Winter Pond are some notable spots. You might also consider a trip to sites like TD Garden or Fenway Park if you have time to see more of the area.
How can I get to and around Winchester?
You can map out your trip in and around Winchester ahead of time with these transportation options. Fly into Bedford, MA (BED-Laurence G. Hanscom Field), which is located 7.7 mi (12.3 km) from the heart of the city. Otherwise, you can search for flights to Boston, MA (BNH-Boston Harbor Seaplane Base), which is 8.4 mi (13.5 km) away. If you’d like to explore around the area, you may want to rent a car for your trip.