Compare Winchester Guest House Rentals

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Featured Guest Houses in Winchester

Copley House

Copley House

3 out of 5
239 W Newton St Boston MA
Free Cancellation
Reserve now, pay when you stay
$90 nightly
The price is $103 total per night
$103 total
Feb 2 - Feb 3
Total with taxes and fees
A local mainstay since 1900, Copley House offers free WiFi in public areas, a computer station, and laundry facilities. Self parking is offered for USD 35 per day. The front desk has multilingual staff that can help with luggage storage, and offer advice about sights and eateries nearby. This smoke-free guesthouse also has a water dispenser.
Oasis Guest House

Oasis Guest House

2.5 out of 5
22 Edgerly Road Boston MA
Free Cancellation
Reserve now, pay when you stay
$113 nightly
The price is $130 total per night
$130 total
Feb 3 - Feb 4
Total with taxes and fees
At Oasis Guest House, guests have access to free WiFi in public areas, coffee in a common area, and a terrace. Self parking is available for USD 25 per night. Front-desk staff can assist with securing valuables and luggage storage.
Beacon Inn 1750

Beacon Inn 1750

3 out of 5
1750 Beacon Street Brookline MA
$104 nightly
The price is $116 total per night
$116 total
Feb 2 - Feb 3
Total with taxes and fees
At Beacon Inn 1750, guests have access to free WiFi in public areas, a business center, and express check-out. Self parking is available for USD 36 per night. Friendly staff can provide concierge services, and also offer advice about sightseeing.
Free WiFi
Air conditioning
Beacon Inn 1087

Beacon Inn 1087

2.5 out of 5
1087 Beacon St Brookline MA
$104 nightly
The price is $116 total per night
$116 total
Feb 2 - Feb 3
Total with taxes and fees
At Beacon Inn 1087, guests have access to free WiFi in public areas, a business center, and express check-out. Self parking is available for USD 36 per night. Helpful staff can provide concierge services and luggage storage.
Free WiFi
Air conditioning
Coolidge Corner Guest House

Coolidge Corner Guest House

3.5 out of 5
17-19 Littell Road Brookline MA
$114 nightly
The price is $128 total per night
$128 total
Feb 2 - Feb 3
Total with taxes and fees
Guests of Coolidge Corner Guest House enjoy access to free WiFi in public areas, coffee in a common area, and microwave in a common area. Self parking is available for USD 18 per day. Additional amenities include a computer station, a library, and free newspapers.
184 Heath St

184 Heath St

2 out of 5
184 Heath St Boston MA
$123 nightly
The price is $141 total per night
$141 total
Feb 2 - Feb 3
Total with taxes and fees
Self parking is available for USD 35 per day.
Pet friendly
Free WiFi
The Inn on the Horse Farm

The Inn on the Horse Farm

3 out of 5
277 Old Sudbury Road Sudbury MA
$99 nightly
The price is $111 total per night
$111 total
Mar 1 - Mar 2
Total with taxes and fees
A local mainstay since 1880, The Inn on the Horse Farm offers free WiFi in public areas, a computer station, and a library. A stay here includes free parking. Friendly staff can provide front-desk service during limited hours, and also offer advice about sightseeing. Additional amenities include express check-out, laundry facilities, and a garden.
Tranquil House in Cambridge

Tranquil House in Cambridge

3 out of 5
15 Holmes Street Cambridge MA
$99 nightly
The price is $113 total per night
$113 total
Feb 2 - Feb 3
Total with taxes and fees
Tranquil House in Cambridge features free WiFi in public areas, coffee in a common area, and a library. Free parking is included with your stay. The front desk has multilingual staff that can help with luggage storage and tours/tickets. Additional amenities include express check-in, express check-out, and a terrace.
Parking included
Free WiFi
Davis Square Inn

Davis Square Inn

3 out of 5
204 Morrison Avenue Somerville MA
A local mainstay since 1873, Davis Square Inn offers free WiFi in public areas, a terrace, and laundry facilities. You can take advantage of free parking if you drive. Additional amenities include a picnic area and a garden.
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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.

Hotel Options in Winchester

    Seaport Hotel Boston

    Seaport Hotel Boston

    1 Seaport Lane Boston MA
    $191 nightly
    The price is $221 total per night from Feb 5 to Feb 6
    $221 total
    Feb 5 - Feb 6
    Total with taxes and fees
    9.6/10 Exceptional! (3,937 reviews)
    Harborside Inn Of Boston

    Harborside Inn Of Boston

    185 State St Boston MA
    $119 nightly
    The price is $139 total per night from Feb 2 to Feb 3
    $139 total
    Feb 2 - Feb 3
    Total with taxes and fees
    9.2/10 Wonderful! (6,178 reviews)
    The Revolution Hotel

    The Revolution Hotel

    40 Berkeley Street Boston MA
    $89 nightly
    The price is $104 total per night from Feb 2 to Feb 3
    $104 total
    Feb 2 - Feb 3
    Total with taxes and fees
    9/10 Wonderful! (2,431 reviews)

Winchester Guest Houses essential information

Accommodation
16 Guest Houses
Lowest Price
$103
Highest Price
$221
Popular accommodation
Copley House, Oasis Guest House, Beacon Inn 1750, Beacon Inn 1087, Coolidge Corner Guest House, 184 Heath St, The Inn on the Horse Farm, Tranquil House in Cambridge, Davis Square Inn