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Family-friendly holiday rentals in West Windsor

Find and book unique family-friendly homes on Airbnb

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Top-rated family-friendly rentals in West Windsor

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Guest favourite
Flat in Springfield
Farm Barn apt. 3 bedr, 2 bath, fiberoptic internet
Getaway for families, couples or groups. Apt. in our Barn. High speed internet, so ideal for "work from home". Full kitchen with oven, microwave, dishwasher, big fridge , 3 bedrooms, 2 baths, Dining/Living room with TV ( Antenna, no cable, Roku: bring your passwords for Netflix..) Fields, forest, hill and river on our property. We allow one friendly dog at a time but it is not allowed to stay in the apt. by itself (daycare in Spgf avbl). Please add the dog to your booking for the one time 35 $.
22–29 May, Individual Host
£92 per night
Guest favourite
Cottage in Hartland
Breeze Hill Cottage
This cozy two bedroom home sits on a rural dirt road overlooking fields, woods, and the NH mountains. Watch birds from the window, relax on the patio, and enjoy the flower gardens. The cottage boasts modern amenities mixed with antiques. Please note: if we don’t respond to an Airbnb message and you need to speak with us, call us on our phones day or night!!! We have had people message us when we were asleep and so we have not been aware and have not responded. Call us! We will hear the phone!
18–25 Feb, Individual Host
£115 per night
Guest favourite
Guest house in Woodstock
Cozy Little Spot (Self Check-in)
Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED. ZERO CONTACT WITH OWNERS.
2–9 May, Individual Host
£142 per night

Popular amenities for West Windsor family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Cabin in Londonderry
The Barn private hot tub/sauna #1 Airbb S. VT
14–21 Dec, Individual Host
£296 per night
Guest favourite
Flat in Townshend
Private Apt. on Farm, great views and Hot tub,
8–15 Aug, Individual Host
£140 per night
Guest favourite
Loft in Ludlow
Spacious Renovated Barn Apt on 100 acres!
7–14 Jan, Professional Host
£304 per night
Guest favourite
Flat in Londonderry
Vermont Getaway Apartment
2–9 Apr, Individual Host
£128 per night
Guest favourite
Home in Plymouth
Top of the World! Jacuzzi! Private Hiking Trails!
7–14 Aug, Individual Host
£414 per night
Guest favourite
Home in Wilmot
Private Creekside Cottage
6–13 Oct, Individual Host
£216 per night
Guest favourite
Home in Ludlow
Ski Chalet with Hot Tub on Okemo Mountain
9–16 May, Individual Host
£324 per night
Guest favourite
Chalet in Killington
Large Chalet; Sauna, Hot Tub; Walk to Trail
8–15 May, Individual Host
£457 per night
Guest favourite
Home in Ludlow
OKEMO GETAWAY Hot Tub & Fire Pit WALK TO TRAILS!
17–24 Jul, Individual Host
£559 per night
Guest favourite
Apartment in Killington
#39: Luxury Ski & Summer Resort & Condo
27 Jul – 3 Aug, Individual Host
£167 per night
Superhost
Apartment in Killington
Come to Killington this Winter!
11–18 Jul, Individual Host
£161 per night
Superhost
Cabin in Sharon
Cozy secluded off-grid cabin ‘birds nest’
19–26 Jul, Individual Host
£220 per night

Family- and pet-friendly home rentals

Guest favourite
Guest house in Springfield
Connecticut River-Cozy Cottage
1–8 May, Individual Host
£82 per night
Guest favourite
Flat in Andover
Private Hilltop farm apartment
15–22 Jun, Individual Host
£101 per night
Guest favourite
Tiny home in Jamaica
Apple Blossom Cottage: A Tiny House
25 Oct – 1 Nov, Individual Host
£100 per night
Guest favourite
Chalet in Stockbridge
Vermont Chalet
18–25 May
£153 per night
Guest favourite
Home in Weston
Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly
2–9 Jun
£147 per night
Guest favourite
Flat in Ludlow
Okemo Vermont Getaway
29 Apr – 6 May, Individual Host
£139 per night
Guest favourite
Chalet in Town of Rockingham
Fantastic Mountain Views, Vermont
4–11 Sept, Individual Host
£223 per night
Guest favourite
Flat in Woodstock
Prospect Place
31 Aug – 7 Sept
£204 per night
Superhost
Cabin in Jamaica
Green Mountain Modern House: iconic modern getaway
8–15 May, Professional Host
£473 per night
Guest favourite
Home in Danby
Comfortable farmhouse with stunning views
21–28 Sept, Individual Host
£159 per night
Guest favourite
Cabin in Woodstock
Cabin by the Stream on 27 Acres
6–13 Jan, Individual Host
£200 per night
Guest favourite
Tiny home in Jamaica
Forest Cabin ~ 7min to Stratton, Cozy, Private
5–12 May, Professional Host
£86 per night

Family-friendly home rentals with a pool

Guest favourite
Apartment in Killington
March dates on Pico 1 bdrm 1 night Ok Free shuttle
7–14 Aug, Individual Host
£167 per night
Superhost
Apartment in Killington
Modern Killington Farmhouse Condo: Close to Resort
2–9 Jul, Professional Host
£246 per night
Guest favourite
Apartment in Killington
Ski, Ride, Walk On/Off Condo On Pico at Killington
10–17 Sept, Individual Host
£204 per night
Guest favourite
Flat in Killington
Family and work friendly Spa at the Woods condo
18–25 Jun, Individual Host
£274 per night
Guest favourite
Guest suite in Killington
Cozy, private, spacious, 3 bedrooms, 5 mi to K Rd.
2–9 Nov, Individual Host
£192 per night
Guest favourite
Apartment in Killington
Top Floor Near Resort 4 Bedroom - Ski In from Mtn
19–26 Apr, Professional Host
£723 per night
Superhost
Apartment in Killington
Killington Escape 2 Story 2BR 2BA Main Building
31 Mar – 7 Apr, Individual Host
£611 per night
Guest favourite
Home in Woodstock
Dana Road House Sunlit VT Country Home w/HotTub
15–22 Jan, Professional Host
£306 per night
Guest favourite
Apartment in Quechee
2 Bedroom Condo in Quechee, VT
4–11 Nov, Individual Host
£125 per night
Guest favourite
Apartment in Ludlow
One Bedroom Suite Near Okemo
18–25 Feb, Individual Host
£179 per night
Guest favourite
Apartment in Quechee
Condo on Quechee Golf Course 3Bd/2Bt Private Feel
26 Apr – 3 May, Individual Host
£300 per night
Guest favourite
Apartment in Killington
⭐️Cozy Ski On-Ski Off Wood Fire Place & King Bed
28 Oct – 4 Nov, Individual Host
£398 per night

Quick stats about holiday rentals that are family-friendly in West Windsor

Total rentals

40 properties

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

10 properties allow pets

Total number of reviews

1.1K reviews

Nightly prices starting at

£71 before taxes and fees

Destinations to explore