Compare Winchester Guest House Rentals

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Featured Guest Houses in Winchester

Blooming Inn

Blooming Inn

3 out of 5
22 Mechanic St Shelburne Falls MA
$143 nightly
The price is $154 total per night
$154 total
Apr 5 - Apr 6
Total with taxes and fees
Blooming Inn features free WiFi in public areas, coffee in a common area, and refrigerator in a common area. You can put free offsite parking to good use if you drive.
Free WiFi
Air conditioning
The Inn At Quail Run

The Inn At Quail Run

2.5 out of 5
106 Smith Road Wilmington VT
Free Cancellation
Reserve now, pay when you stay
$195 nightly
The price is $215 total per night
$215 total
Apr 13 - Apr 14
Total with taxes and fees
The Inn At Quail Run features a sauna, free WiFi in public areas, and a hot tub. If you plan to drive, free parking is available. Additional amenities include a seasonal outdoor pool, a microwave in a common area, and a refrigerator in a common area.
Pool
Hot Tub
The Burrell House

The Burrell House

2.5 out of 5
112 Washington St Keene NH
$133 nightly
The price is $144 total per night
$144 total
Apr 6 - Apr 7
Total with taxes and fees
The Burrell House features free WiFi in public areas and a picnic area. If you decide to drive, there's free parking.
Parking included
Free WiFi
In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony

Shelburne Falls MA
$140 nightly
The price is $156 total per night
$156 total
Apr 14 - Apr 15
Total with taxes and fees
This guesthouse features free WiFi in public areas and a garden.
Free WiFi
Air conditioning
Relax in a Unique Treehouse Getaway - in Southwest NH

Relax in a Unique Treehouse Getaway - in Southwest NH

Munsonville NH
$302 nightly
The price is $328 total per night
$328 total
Apr 5 - Apr 6
Total with taxes and fees
At this guesthouse, guests have access to features like local meal delivery service. This smoke-free guesthouse also has a garden.
Free WiFi
Air conditioning
Pristine Magical Retreat Cottage - 15 min to Mt Snow skiing

Pristine Magical Retreat Cottage - 15 min to Mt Snow skiing

East Dover VT
Guests staying at this guesthouse have access to laundry facilities, a living plant wall, and a garden. This smoke-free guesthouse also has barbecue grills.
Pool
Free WiFi
Angels Rest Retreat

Angels Rest Retreat

3 out of 5
63 North County Road Leyden MA
Guests staying at Angels Rest Retreat enjoy an outdoor pool, 2 hot tubs, and free WiFi in public areas. If you drive, take advantage of free parking. Additional amenities include conference space, coffee/tea in a common area, and a terrace.
Pool
Hot Tub
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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

    The Colonial Hotel

    The Colonial Hotel

    625 Betty Spring Road Gardner MA
    $160 nightly
    The price is $179 total per night from Apr 5 to Apr 6
    $179 total
    Apr 5 - Apr 6
    Total with taxes and fees
    8.8/10 Excellent! (1,000 reviews)
    Colonial Motel And Spa

    Colonial Motel And Spa

    889 Putney Rd Brattleboro VT
    $100 nightly
    The price is $110 total per night from Apr 5 to Apr 6
    $110 total
    Apr 5 - Apr 6
    Total with taxes and fees
    6.8/10 (1,001 reviews)
    Hampton Inn Brattleboro

    Hampton Inn Brattleboro

    1378 Putney Road Brattleboro VT
    $130 nightly
    The price is $143 total per night from Apr 10 to Apr 11
    $143 total
    Apr 10 - Apr 11
    Total with taxes and fees
    8.2/10 Very Good! (955 reviews)

Winchester Guest Houses essential information

Accommodation
7 Guest Houses
Lowest Price
$110
Highest Price
$328
Popular accommodation
Blooming Inn, The Inn At Quail Run, The Burrell House, In town, newly remodeled studio with private balcony , Relax in a Unique Treehouse Getaway - in Southwest NH, Pristine Magical Retreat Cottage - 15 min to Mt Snow skiing, Angels Rest Retreat

More to Explore