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
$124 nightly
The price is $133 total per night
$133 total
Nov 4 - Nov 5
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 Burrell House

The Burrell House

2.5 out of 5
112 Washington St Keene NH
$141 nightly
The price is $153 total per night
$153 total
Oct 21 - Oct 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
Inn at Valley Farms

Inn at Valley Farms

2 out of 5
633 Wentworth Rd Walpole NH
$177 nightly
The price is $192 total per night
$192 total
Oct 29 - Oct 30
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
In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony

Shelburne Falls MA
$171 nightly
The price is $191 total per night
$191 total
Oct 21 - Oct 22
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
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $186 total per night
$186 total
Nov 2 - Nov 3
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
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
Nov 1 - Nov 2
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
$310 nightly
The price is $336 total per night
$336 total
Oct 6 - Oct 7
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, a garden, and barbecue grills. This smoke-free guesthouse also has a living plant wall.
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

    2 private mountain RV pads for rent. Full hook ups

    2 private mountain RV pads for rent. Full hook ups

    Winchester NH
    $75 nightly
    The price is $81 total per night from Oct 5 to Oct 6
    $81 total
    Oct 5 - Oct 6
    Total with taxes and fees
    Colonial Motel

    Colonial Motel

    889 Putney Rd Brattleboro VT
    $84 nightly
    The price is $93 total per night from Nov 1 to Nov 2
    $93 total
    Nov 1 - Nov 2
    Total with taxes and fees
    6.6/10 (73 reviews)
    The Colonial Hotel

    The Colonial Hotel

    625 Betty Spring Road Gardner MA
    $144 nightly
    The price is $161 total per night from Nov 1 to Nov 2
    $161 total
    Nov 1 - Nov 2
    Total with taxes and fees
    8.8/10 Excellent! (1,002 reviews)

Winchester Guest Houses essential information

Accommodation
9 Guest Houses
Lowest Price
$81
Highest Price
$336
Popular accommodation
Blooming Inn, The Burrell House, Inn at Valley Farms, In town, newly remodeled studio with private balcony , Cooper Hill Inn, 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