Waterfront holiday rentals in Windsor County
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Top-rated waterfront accommodation in Windsor County
Guests agree: These waterfront accommodation options are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Windsor County waterfront rentals
Waterfront apartment accommodation
Apartment in Wallingford
5.0 out of 5 average rating, 28 reviews49 River Street
28 Sep – 5 Oct
Apartment in Chester
4.9 out of 5 average rating, 49 reviewsSpacious, Sunny, Second Story 2 Bedroom Apartment
13–20 Dec
Apartment in Bridgewater
4.67 out of 5 average rating, 100 reviewsComfortable ski getaway in the heart of it all!
30 Nov – 7 Dec
Apartment in Woodstock
5.0 out of 5 average rating, 19 reviewsVermont Getaway in historic Woodstock VT
16–23 Oct
Apartment in Lebanon
New place to stayWest Leb Studio with Loft
16–23 May
Apartment in Cavendish
4.93 out of 5 average rating, 43 reviewsMurphys4Seasons Studio Proctorsville
8–15 Aug
Apartment in Hartland
4.67 out of 5 average rating, 24 reviewsPrivate Riverside Studio* Upper Valley*Vermont
7–14 Sep
Apartment in Hartford
New place to stayThe Maple Street Flats: A
12–19 Nov
Waterfront house rentals
Home in Woodstock
4.98 out of 5 average rating, 45 reviewsPet Friendly Woodstock Home; Riverside Getaway!
13–20 Oct
Home in Plymouth
4.75 out of 5 average rating, 357 reviewsBEST OF LAKE FRONT LIVING, HOT TUB & FIREPIT !!
26 Sep – 3 Oct
Home in Woodstock
4.9 out of 5 average rating, 62 reviewsBrookside Farm, Woodstock, VT - 18 ac. with barn
17–24 Sep
Home in Ludlow
4.94 out of 5 average rating, 82 reviewsOKEMO LAKE FRONT (Lake Rescue) ALL SEASON HOUSE
5–12 Apr
Home in Woodstock
5.0 out of 5 average rating, 15 reviewsGrange Hall, South Woodstock Historic Home
25 Jul – 1 Aug
Home in Bridgewater
4.75 out of 5 average rating, 104 reviewsThe Buddah House
25 Jul – 1 Aug
Home in Strafford
5.0 out of 5 average rating, 19 reviewsRenovated Farmhouse: serene, modern & private
18–25 Oct
Home in Windsor
5.0 out of 5 average rating, 10 reviewsKennedy’s House
22–29 May
Waterfront condo accommodation
Condo in Hartford
5.0 out of 5 average rating, 6 reviews3 Bedroom condo with beautiful golf course views
5–12 Dec
Condo in Hartford
5 Minute walk to Lake Pineo
1–8 Nov
Condo in Ludlow
4.64 out of 5 average rating, 28 reviews2BR Riverfront 2nd-Floor | Balcony |
26 Jun – 3 Jul
Condo in Hartford
Golfer's Paradise
11–18 Oct
Condo in Plymouth
4.64 out of 5 average rating, 70 reviewsSpacious 4BR Lakefront | Deck | Pool
7–14 Jun
Destinations to explore
- Waterfront rentals United States
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- Apartment rentals Windsor County
- Bed and breakfasts Windsor County
- Rentals with pools Windsor County
- Rentals with lake access Windsor County
- Pet-friendly rentals Windsor County
- Condo rentals Windsor County
- Rentals with a washing machine and dryer Windsor County
- Cabin rentals Windsor County
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- Rentals with a hot tub Windsor County
- Cottage rentals Windsor County
- Ski-in/ski-out rentals Windsor County
- Rentals with outdoor seating Windsor County
- Tiny house rentals Windsor County
- Rentals with a sauna Windsor County
- Rentals with a patio Windsor County
- Farmstay rentals Windsor County
- Rentals with an EV charger Windsor County
- Rentals with a fire pit Windsor County
- Kid-friendly rentals Windsor County
- Guesthouse rentals Windsor County
- House rentals Windsor County
- Private suite rentals Windsor County
- Family-friendly rentals Windsor County
- Townhouse rentals Windsor County
- Rentals with breakfast Windsor County
- Rentals with a kayak Windsor County
- Beachfront rentals Windsor County
- Rentals with an accessible height bed Windsor County
- Rentals with an accessible height toilet Windsor County
- Rentals with a fireplace Windsor County
- Monthly Rentals Windsor County
- Villa rentals Windsor County
- Rentals with beach access Windsor County
- Fitness-friendly rentals Windsor County
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