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
$146 nightly
The price is $158 total per night
$158 total
Jul 6 - Jul 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
Inn at Valley Farms

Inn at Valley Farms

2 out of 5
633 Wentworth Rd Walpole NH
$200 nightly
The price is $217 total per night
$217 total
Jul 19 - Jul 20
Total with taxes and fees
Guests staying at Inn at Valley Farms enjoy free WiFi in public areas, express check-out, and a garden. Free parking is available if you drive. Additional amenities include barbecue grills and a picnic area.
Parking included
Free WiFi
Blooming Inn

Blooming Inn

3 out of 5
22 Mechanic St Shelburne Falls MA
$140 nightly
The price is $150 total per night
$150 total
Jul 5 - Jul 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
In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony

Shelburne Falls MA
$144 nightly
The price is $161 total per night
$161 total
Jul 7 - Jul 8
Total with taxes and fees
This guesthouse features free WiFi in public areas and a garden.
Free WiFi
Air conditioning
Cooper Hill Inn

Cooper Hill Inn

2 out of 5
117 Cooper Hill Rd West Dover VT
$186 nightly
The price is $205 total per night
$205 total
Jul 27 - Jul 28
Total with taxes and fees
At Cooper Hill Inn, guests have access to free WiFi in public areas, a terrace, and laundry facilities. A stay here includes free parking. Additional amenities include a garden and barbecue grills.
Parking included
Free WiFi
Handcrafted NH Treehouse · 2hr Boston · Fire Pit, Lake, Stargazing

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

Munsonville NH
$310 nightly
The price is $336 total per night
$336 total
Jul 13 - Jul 14
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
The Inn At Quail Run

The Inn At Quail Run

2.5 out of 5
106 Smith Road Wilmington VT
$225 nightly
The price is $248 total per night
$248 total
Jul 5 - Jul 6
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
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, a living plant wall, and barbecue grills. 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

Winchester Guest Houses essential information

Accommodation
9 Guest Houses
Lowest Price
$81
Highest Price
$336
Popular accommodation
The Burrell House, Inn at Valley Farms, Blooming Inn, In town, newly remodeled studio with private balcony , Cooper Hill Inn, Handcrafted NH Treehouse · 2hr Boston · Fire Pit, Lake, Stargazing, The Inn At Quail Run, Pristine Magical Retreat Cottage - 55% off monthly, 15% off weekly till June 20., Angels Rest Retreat

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