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
$192 nightly
The price is $209 total per night
$209 total
Jan 8 - Jan 9
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
$139 nightly
The price is $150 total per night
$150 total
Jan 4 - Jan 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
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
Jan 5 - Jan 6
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
$225 nightly
The price is $248 total per night
$248 total
Jan 6 - Jan 7
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
Relax in a Unique Treehouse Getaway - in Southwest NH

Relax in a Unique Treehouse Getaway - in Southwest NH

Munsonville NH
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
Magical Retreat Cottage - Brilliant Autumn Colors and Waterfalls Vermont Getaway

Magical Retreat Cottage - Brilliant Autumn Colors and Waterfalls Vermont Getaway

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

    The Colonial Hotel

    The Colonial Hotel

    625 Betty Spring Road Gardner MA
    $160 nightly
    The price is $179 total per night from Jan 4 to Jan 5
    $179 total
    Jan 4 - Jan 5
    Total with taxes and fees
    8.8/10 Excellent! (1,003 reviews)
    The Covered Bridge Inn

    The Covered Bridge Inn

    1043 Putney Road Brattleboro VT
    $79 nightly
    The price is $87 total per night from Jan 4 to Jan 5
    $87 total
    Jan 4 - Jan 5
    Total with taxes and fees
    7.6/10 Good! (1,003 reviews)
    Comfort Inn & Suites Brattleboro I-91

    Comfort Inn & Suites Brattleboro I-91

    1186 Putney Road Brattleboro VT
    $140 nightly
    The price is $154 total per night from Jan 20 to Jan 21
    $154 total
    Jan 20 - Jan 21
    Total with taxes and fees
    8.4/10 Very Good! (749 reviews)

Winchester Guest Houses essential information

Accommodation
7 Guest Houses
Lowest Price
$87
Highest Price
$248
Popular accommodation
The Burrell House, Blooming Inn, In town, newly remodeled studio with private balcony , The Inn At Quail Run, Relax in a Unique Treehouse Getaway - in Southwest NH, Magical Retreat Cottage - Brilliant Autumn Colors and Waterfalls Vermont Getaway, Angels Rest Retreat

More to Explore