Compare Winchester Guest House Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Guest Houses in Winchester

The Burrell House

The Burrell House

2.5 out of 5
112 Washington St Keene NH
$129 nightly
The price is $140 total per night
$140 total
Aug 23 - Aug 24
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
$143 nightly
The price is $154 total per night
$154 total
Aug 27 - Aug 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
Handcrafted NH Treehouse · 2hr Boston · Fire Pit, Lake, Stargazing

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

Munsonville NH
$313 nightly
The price is $340 total per night
$340 total
Aug 19 - Aug 20
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.
Inn at Valley Farms

Inn at Valley Farms

2 out of 5
633 Wentworth Rd Walpole NH
$208 nightly
The price is $226 total per night
$226 total
Aug 20 - Aug 21
Total with taxes and fees
Guests staying at Inn at Valley Farms enjoy free WiFi in public areas, express check-out, and barbecue grills. Free parking is available if you drive. Additional amenities include a picnic area and a garden.
Parking included
Free WiFi
In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony

Shelburne Falls MA
$150 nightly
The price is $168 total per night
$168 total
Sep 1 - Sep 2
Total with taxes and fees
This guesthouse features free WiFi in public areas and a garden.
Cooper Hill Inn

Cooper Hill Inn

2 out of 5
117 Cooper Hill Rd West Dover VT
$207 nightly
The price is $228 total per night
$228 total
Aug 19 - Aug 20
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.
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
Aug 19 - Aug 20
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.
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.
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
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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 Aug 19 to Aug 20
    $81 total
    Aug 19 - Aug 20
    Total with taxes and fees
    The Colonial Hotel

    The Colonial Hotel

    625 Betty Spring Road Gardner MA
    $170 nightly
    The price is $190 total per night from Aug 19 to Aug 20
    $190 total
    Aug 19 - Aug 20
    Total with taxes and fees
    9/10 Wonderful! (1,005 reviews)
    Keene Elm City Hotel, an Ascend Collection Hotel

    Keene Elm City Hotel, an Ascend Collection Hotel

    175 Key Rd Keene NH
    $120 nightly
    The price is $130 total per night from Sep 1 to Sep 2
    $130 total
    Sep 1 - Sep 2
    Total with taxes and fees
    8.6/10 Excellent! (1,007 reviews)

Winchester Guest Houses essential information

Accommodation
9 Guest Houses
Lowest Price
$81
Highest Price
$340
Popular accommodation
The Burrell House, Blooming Inn, Handcrafted NH Treehouse · 2hr Boston · Fire Pit, Lake, Stargazing, Inn at Valley Farms, In town, newly remodeled studio with private balcony , Cooper Hill Inn, The Inn At Quail Run, Pristine Magical Retreat Cottage - 55% off monthly, 15% off weekly till June 20., Angels Rest Retreat

More to Explore