Compare Winchester Guest House Rentals

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Featured Guest Houses in Winchester

The Burrell House

The Burrell House

2.5 out of 5
112 Washington St Keene NH
$140 nightly
The price is $151 total per night
$151 total
May 21 - May 22
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
Blooming Inn

Blooming Inn

3 out of 5
22 Mechanic St Shelburne Falls MA
$156 nightly
The price is $169 total per night
$169 total
May 27 - May 28
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
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
Jun 1 - Jun 2
Total with taxes and fees
This guesthouse features free WiFi in public areas and a garden.
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
May 21 - May 22
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
Handcrafted NH Treehouse · 2hr Boston · Fire Pit, Lake, Stargazing

Handcrafted NH Treehouse · 2hr Boston · Fire Pit, Lake, Stargazing

Munsonville NH
$308 nightly
The price is $334 total per night
$334 total
May 21 - May 22
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 - 55% off monthly, 15% off weekly till June 20.

Pristine Magical Retreat Cottage - 55% off monthly, 15% off weekly till June 20.

East Dover VT
Guests staying at this guesthouse have access to laundry facilities, barbecue grills, and a living plant wall. This smoke-free guesthouse also has a garden.
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 May 25 to May 26
    $179 total
    May 25 - May 26
    Total with taxes and fees
    8.8/10 Excellent! (1,004 reviews)
    Hampton Inn Brattleboro

    Hampton Inn Brattleboro

    1378 Putney Road Brattleboro VT
    $122 nightly
    The price is $134 total per night from Jun 7 to Jun 8
    $134 total
    Jun 7 - Jun 8
    Total with taxes and fees
    8.2/10 Very Good! (978 reviews)
    Latchis Hotel

    Latchis Hotel

    50 Main Street Brattleboro VT
    $116 nightly
    The price is $128 total per night from May 26 to May 27
    $128 total
    May 26 - May 27
    Total with taxes and fees
    8.6/10 Excellent! (883 reviews)

Winchester Guest Houses essential information

Accommodation
7 Guest Houses
Lowest Price
$128
Highest Price
$334
Popular accommodation
The Burrell House, Blooming Inn, In town, newly remodeled studio with private balcony , The Inn At Quail Run, Handcrafted NH Treehouse · 2hr Boston · Fire Pit, Lake, Stargazing, Pristine Magical Retreat Cottage - 55% off monthly, 15% off weekly till June 20., Angels Rest Retreat

More to Explore