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
$151 nightly
The price is $164 total per night
$164 total
Oct 15 - Oct 16
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
Oct 5 - Oct 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
The Inn At Quail Run

The Inn At Quail Run

2.5 out of 5
106 Smith Road, Wilmington, VT
$185 nightly
The price is $204 total per night
$204 total
Nov 1 - Nov 2
Total with taxes and fees
Guests staying at The Inn At Quail Run enjoy a 24-hour gym, a sauna, and free WiFi in public areas. 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
Parking included
In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony

$140 nightly
The price is $156 total per night
$156 total
Oct 26 - Oct 27
Total with taxes and fees
This guesthouse features free WiFi in public areas and a garden.
Free WiFi
Air conditioning
Relax in a Unique Treehouse Getaway - in Southwest NH

Relax in a Unique Treehouse Getaway - in Southwest 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

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 Oct 20 to Oct 21
    $179 total
    Oct 20 - Oct 21
    Total with taxes and fees
    8.8/10 Excellent! (1,016 reviews)
    Econo Lodge Brattleboro

    Econo Lodge Brattleboro

    515 Canal St, Brattleboro, VT
    $68 nightly
    The price is $75 total per night from Nov 2 to Nov 3
    $75 total
    Nov 2 - Nov 3
    Total with taxes and fees
    5.4/10 (568 reviews)
    Keene Elm City Hotel, an Ascend Collection Hotel

    Keene Elm City Hotel, an Ascend Collection Hotel

    175 Key Rd, Keene, NH
    $107 nightly
    The price is $116 total per night from Nov 2 to Nov 3
    $116 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.4/10 Very Good! (908 reviews)

Winchester Guest Houses essential information

Accommodation
7 Guest Houses
Lowest Price
$75
Highest Price
$204
Popular accommodation
The Burrell House, Blooming Inn, The Inn At Quail Run, In town, newly remodeled studio with private balcony , Relax in a Unique Treehouse Getaway - in Southwest NH, Magical Retreat Cottage - Brilliant Autumn Colors and Waterfalls Vermont Getaway, Angels Rest Retreat

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