Family-friendly holiday rentals in West Windsor

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in West Windsor

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

Guest favourite
Apartment 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 $.
30 Apr – 7 May
4.9 out of 5 average rating, 219 reviews
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!
9 – 16 July
4.97 out of 5 average rating, 415 reviews
Guest favourite
Guesthouse in Springfield
Connecticut River-Cozy Cottage
This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.
30 Oct – 6 Nov
4.86 out of 5 average rating, 321 reviews

Popular amenities for West Windsor family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Apartment in Townshend
Private Apt. on Farm, great views and Hot tub,
4 – 11 Apr
4.93 out of 5 average rating, 198 reviews
Guest favourite
Apartment in Londonderry
Vermont Getaway Apartment
30 July – 6 Aug
4.97 out of 5 average rating, 546 reviews
Guest favourite
Loft in Ludlow
Spacious Renovated Barn Apt on 100 acres!
5 – 12 Jan
4.95 out of 5 average rating, 724 reviews
Guest favourite
Condo in Killington
#39: Luxury Ski & Summer Resort & Condo
24 – 31 May
4.97 out of 5 average rating, 188 reviews
Guest favourite
Home in Ludlow
Ski Chalet with Hot Tub on Okemo Mountain
27 May – 3 June
4.97 out of 5 average rating, 143 reviews
Guest favourite
Home in Plymouth
Top of the World! Jacuzzi! Private Hiking Trails!
26 Mar – 2 Apr
4.95 out of 5 average rating, 220 reviews
Superhost
Cabin in Londonderry
The Barn private hot tub/sauna #1 Airbb S. VT
27 Sept – 4 Oct
4.82 out of 5 average rating, 416 reviews
Guest favourite
Chalet in Killington
Large Chalet; Sauna, Hot Tub; Walk to Trail
3 – 10 June
4.87 out of 5 average rating, 223 reviews
Guest favourite
Home in Ludlow
OKEMO GETAWAY Hot Tub & Fire Pit WALK TO TRAILS!
26 July – 2 Aug
4.93 out of 5 average rating, 137 reviews
Guest favourite
Chalet in Killington
Close to Mountain and walk to restaurants!
2 – 7 July
4.9 out of 5 average rating, 154 reviews
Guest favourite
Chalet in Killington
Luxury, AC, 6 BR, 12 Beds, 3 Bath, Hot Tub, Yard
2 – 9 Oct
5.0 out of 5 average rating, 117 reviews
Guest favourite
Chalet in Killington
Killington Chalet - Hot Tub, Sauna, Boot Dryer
28 Nov – 5 Dec
4.82 out of 5 average rating, 232 reviews

Family- and pet-friendly home rentals

Guest favourite
Apartment in Andover
Private Hilltop farm apartment
5 – 12 May
4.98 out of 5 average rating, 381 reviews
Guest favourite
Tiny home in Jamaica
Apple Blossom Cottage: A Tiny House
22 Feb – 1 Mar
4.94 out of 5 average rating, 1127 reviews
Guest favourite
Apartment in Ludlow
Okemo Vermont Getaway
21 – 28 Apr
4.92 out of 5 average rating, 250 reviews
Guest favourite
Chalet in Stockbridge
Vermont Chalet
17 – 24 Aug
4.84 out of 5 average rating, 108 reviews
Guest favourite
Apartment in Woodstock
Prospect Place
2 – 9 Nov
4.94 out of 5 average rating, 102 reviews
Guest favourite
Cottage in Brandon
Henrietta’s Hideaway-Walk Downtown!
29 Apr – 6 May
4.91 out of 5 average rating, 260 reviews
Guest favourite
Home in Weston
Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly
29 May – 5 June
4.95 out of 5 average rating, 218 reviews
Guest favourite
Home in Danby
Comfortable farmhouse with stunning views
12 – 19 July
4.97 out of 5 average rating, 194 reviews
Guest favourite
Chalet in Town of Rockingham
Fantastic Mountain Views, Vermont
11 – 18 Apr
4.96 out of 5 average rating, 109 reviews
Guest favourite
Cabin in Woodstock
Cabin by the Stream on 27 Acres
18 – 25 Feb
4.96 out of 5 average rating, 191 reviews
Guest favourite
Guest suite in Mt Holly
Exquisite Green Mountain Loft Haven
5 – 12 Sept
4.98 out of 5 average rating, 117 reviews
Guest favourite
Tiny home in Jamaica
Forest Cabin ~ 7min to Stratton, Cozy, Private
22 – 29 Apr
4.89 out of 5 average rating, 340 reviews

Family-friendly home rentals with a pool

Guest favourite
Condo in Killington
March dates on Pico 1 bdrm 1 night Ok Free shuttle
11 – 18 June
4.93 out of 5 average rating, 379 reviews
Superhost
Condo in Ludlow
Enjoy a Ski-On/Ski-Off Okemo Ski Getaway
15 – 22 Apr
4.79 out of 5 average rating, 143 reviews
Superhost
Condo in Killington
A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532
25 Apr – 2 May
4.9 out of 5 average rating, 229 reviews
Guest favourite
Condo in Killington
Ski, Ride, Walk On/Off Condo On Pico at Killington
23 – 30 Oct
4.82 out of 5 average rating, 245 reviews
Guest favourite
Apartment in Killington
Family and work friendly Spa at the Woods condo
15 – 22 May
4.92 out of 5 average rating, 119 reviews
Guest favourite
Guest suite in Killington
Cozy, private, spacious, 3 bedrooms, 5 mi to K Rd.
19 – 26 Feb
4.95 out of 5 average rating, 138 reviews
Guest favourite
Condo in Killington
Top Floor Near Resort 4 Bedroom - Ski In from Mtn
19 – 26 Jan
4.86 out of 5 average rating, 104 reviews
Superhost
Condo in Killington
Killington Escape 2 Story 2BR 2BA Main Building
19 – 26 May
4.79 out of 5 average rating, 100 reviews
Superhost
Condo in Killington
Amazing,Ski, Golf, Hike, Bike, Adventures
8 – 15 Feb
4.78 out of 5 average rating, 160 reviews
Guest favourite
Home in Woodstock
Dana Road House Sunlit VT Country Home w/HotTub
3 – 10 May
4.98 out of 5 average rating, 52 reviews
Guest favourite
Condo in Quechee
2 Bedroom Condo in Quechee, VT
5 – 12 May
4.9 out of 5 average rating, 68 reviews
Guest favourite
Condo in Ludlow
One Bedroom Suite Near Okemo
19 – 26 Mar
4.89 out of 5 average rating, 74 reviews

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

$138 AUD before taxes and fees

Destinations to explore