Vacation rentals in Londonderry

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Top-rated vacation rentals in Londonderry

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite

Cabin in Londonderry

4.93 out of 5 average rating, 308 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond in S Londonderry, VT. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery and hiking right outside your front door. The Cabin has an open floor plan with a galley kitchen, dining/living area with pullout futon couch & 1 full bathroom. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Oct. 4 – 11

$164 CAD per night
Guest favourite

Cottage in Jamaica

4.82 out of 5 average rating, 461 reviews

Forest Cottage ~ 7min to Stratton, Private, Views

Authentic Vermont post & beam cottage with privacy. 3 miles to Stratton's Sun Bowl, a 7-minute drive. Nearby swimming hole at the brook on the property. Dogs welcome, $30 fee per dog. No cats due to allergies. Vinyl record player, VCR/DVD player, board games, Starlink Satellite Internet 20-100 mbps. Heat options: 2 gas wall furnaces & wood stove. Front porch, propane BBQ, fire pit, picnic table & spectacular views of Stratton Mountain. Back deck surrounded by woods with hammock, table & chairs.

May 8 – 15

$183 CAD per night
Guest favourite

Cottage in Londonderry

4.96 out of 5 average rating, 199 reviews

Vermont Treehouse - Romantic Private Elegant

SPECIAL 2 night minimum, self checkin. Work remotely. Enjoy this romantic, elegant, private getaway for two (or one) in our "Treehouse" with sleeping loft, full kitchen & bathroom, screened porch, deck, sauna, WiFi, BBQ grill, etc. Overlooking pasture & mountains. Enjoy the property with 3 miles hiking/snowshoe trails on property. Guest house on 160 acre private horse farm. Lots to do at nearby ski areas, shopping, hiking, biking, theater in summer. Or just relax. Discount for longer stays.

Oct. 19 – 26

$536 CAD per night

Popular amenities for Londonderry vacation rentals

Stay near Londonderry's top sights

Magic Mountain Ski Area136 locals recommend
Winhall Brook Campground4 locals recommend
Honeypie122 locals recommend
Jamaica Cottage Shop, Inc.3 locals recommend
Clark's Quality Foods Londonderry VT45 locals recommend
Jake's Restaurant and Tavern35 locals recommend

Other great vacation rentals in Londonderry

Guest favourite

Guesthouse in Pawlet

4.91 out of 5 average rating, 282 reviews

Picturesque Cabin on the Mettowee

Jan. 17 – 24

$178 CAD per night
Guest favourite

Apartment in Manchester

5.0 out of 5 average rating, 142 reviews

Private two-bedroom suite within a two-story house

Apr. 14 – 21

$152 CAD per night
Superhost

Cabin in Londonderry

4.82 out of 5 average rating, 419 reviews

The Honeymoon Barn - hot tub/sauna #1 Airbb S. VT

Dec. 1 – 8

$509 CAD per night
Guest favourite

Condo in Londonderry

4.95 out of 5 average rating, 42 reviews

Magical Ski-In/Ski-Out Condo at Magic w/ game room

Jun. 21 – 28

$180 CAD per night
Guest favourite

Apartment in Londonderry

4.95 out of 5 average rating, 22 reviews

Dog-friendly, 1-bedroom apartment w/ fireplace (B)

Sep. 22 – 29

$205 CAD per night
Guest favourite

Cabin in Londonderry

4.96 out of 5 average rating, 95 reviews

Summit view cottage: Secluded cabin with hot tub

Oct. 30 – Nov. 6

$658 CAD per night
Guest favourite

Tiny homes in Athens

4.93 out of 5 average rating, 28 reviews

LUXE Forest Retreat

Aug. 8 – 15

$492 CAD per night
Guest favourite

Chalet in Londonderry

4.98 out of 5 average rating, 90 reviews

Modern 3-bedroom A-frame in Londonderry, VT

Oct. 30 – Nov. 6

$772 CAD per night
Guest favourite

Cabin in Londonderry

4.93 out of 5 average rating, 74 reviews

Deerwood Hill Cabin, Hot Tub, Ski, Epic Fireplace

Jun. 28 – Jul. 5

$722 CAD per night
Guest favourite

Apartment in Weston

5.0 out of 5 average rating, 22 reviews

Peaceful Woods- Suite with Private Entrance

Sep. 7 – 14

$210 CAD per night
Guest favourite

Guesthouse in Grafton

4.89 out of 5 average rating, 90 reviews

VT Sugar House-Guesthouse

Oct. 22 – 29

$114 CAD per night
Guest favourite

Condo in Stratton

4.91 out of 5 average rating, 44 reviews

Stratton Mountain vacation spot

Jun. 8 – 15

$174 CAD per night

Quick stats about vacation rentals in Londonderry

Total rentals

170 properties

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

70 properties allow pets

Family-friendly rentals

140 properties are a good fit for families

Total number of reviews

7.8K reviews

Nightly prices starting at

$109 CAD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windham County
  5. Londonderry