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1,000 Rentals In Windsor Area
United States
Vermont
Windsor Area
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Sub Areas
Plymouth
(10)
Bridgewater
(8)
Stockbridge
(3)
Guests
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1
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Price
Per Night:
Amenities
Pool
Internet
Washer
Fishing
FirePlace
Wheelchair Access
Non Smoking
Yard
TV
Balcony
Patio
Parking
AC
Microwave
No Pets
Jacuzzi
Pet Allowed
Dishwasher
Kitchen
Sauna
Crib
Smoking Allowed
Grill
Songbird Haven–majestic VT Timberframe, Dog-Friendly Home Along The White River
4
3.0
10
Rochester Vermont Private vacation home
From $608 per night
(USD)
Clean, Updated, & Well Appointed-Family & Dog Friendly Rental
2
2.0
6
Ludlow Vermont Apartment
From $194 per night
(USD)
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town
2
1.0
4
Woodstock Vermont Private vacation home
From $547 per night
(USD)
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
2
2.0
6
Ludlow Vermont Apartment
From $285 per night
(USD)
Charming Log Cabin Apartment in Woodstock Village
1
1.0
4
Woodstock Vermont Apartment
From $255 per night
(USD)
Reading Farms Estate
15
13.0
46
Reading Vermont Private vacation home
From $4094 per night
(USD)
Luxury 3BR Cabin 5 min Drive to Okemo and on Ski Shuttle Route
3
2.0
6
Ludlow Vermont Private vacation home
From $650 per night
(USD)
Beautiful 3000 Square Foot Home
5
3.0
10
Cavendish Vermont Cabin
From $614 per night
(USD)
Luxury Farmhouse Retreat with Jacuzzi, Skate/Swim Pond & AC!
7
3.0
28
Bridgewater Vermont Private vacation home
From $752 per night
(USD)
Winterplace at Okemo Mountain
2
2.0
9
Ludlow Vermont Condo
From $297 per night
(USD)
Luxurious, Secluded, Ski Chalet, w/ Country Decor & Hot Tub Near Okemo
4
3.0
12
Ludlow Vermont Private vacation home
From $724 per night
(USD)
Room in Historic Inn! 20 Minutes to Okemo!
1
1.0
3
Chester Vermont Bed & breakfast
From $167 per night
(USD)
King & Queen Suite in Historic Inn Circa 1780
1
1.0
6
Chester Vermont Bed & breakfast
From $200 per night
(USD)
Ludlow Home w/ Hot Tub, Near Okemo Resort!
4
3.0
11
Ludlow Vermont Private vacation home
From $508 per night
(USD)
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
3
2.0
8
Bridgewater Vermont Private vacation home
From $413 per night
(USD)
Secluded 2600 sq ft home 15 min from Okemo+Killington
4
4.0
8
Plymouth Vermont Private vacation home
From $473 per night
(USD)
Stunning Winter Ski, Summer Lake and Fall leaf-peeping home.
3
1.0
8
Ludlow Vermont Private vacation home
From $996 per night
(USD)
Ski House on Lake Rescue, 3.5 Miles from Okemo
4
3.0
8
Ludlow Vermont Private vacation home
From $462 per night
(USD)
Great 4BR/3BA for families in village w/ easy shuttle access. Read our reviews!
4
3.0
12
Ludlow Vermont Condo
From $451 per night
(USD)
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
3
2.0
6
Ludlow Vermont Cabin
From $340 per night
(USD)
Private Quechee House near the Club & Golf
4
4.0
8
Woodstock Vermont Private vacation home
Click For Pricing
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,
3
1.0
6
Ludlow Vermont Chalet
From $704 per night
(USD)
Great Location, Large Hot Tub, Wet Bar, Pool Table, Gas FP
5
4.0
16
Ludlow Vermont Private vacation home
From $839 per night
(USD)
Custom Luxury Home w/Hot Tub on Okemo Mtn/Family/Group Friendly/Shuttle Bus
6
4.0
12
Ludlow Vermont Private vacation home
From $2453 per night
(USD)
Ludlow Vermont Ski House
4
2.0
8
Ludlow Vermont Private vacation home
From $1388 per night
(USD)
Sunlit VT Country Home w/Hot Tub. Ideal location near Woodstock village
3
2.0
6
Woodstock Vermont Private vacation home
From $514 per night
(USD)
Delightful Cozy Space in Woodstock Village
1
1.0
4
Woodstock Vermont Apartment
From $329 per night
(USD)
6-Bedroom Peaceful and Private Retreat in Scenic Quechee, Vermont
6
3.0
8
Hartford Vermont Private vacation home
From $982 per night
(USD)
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
1
1.0
4
Hartland Vermont Cabin
From $473 per night
(USD)
Fabulous 10 BR, 5 Bath, 5 min to OKEMO Mtn, on Shuttle Rte, Hot Tub, King
10
5.0
30
Ludlow Vermont Private vacation home
From $1401 per night
(USD)
\"The Crooked House\" with A/C and sauna on private wooded lot near Killington
3
2.0
8
Stockbridge Vermont Private vacation home
From $416 per night
(USD)
School Brick House is the perfect location for a vacation
3
2.0
6
Rochester Vermont Private vacation home
From $298 per night
(USD)
Beautiful Modern Cabin on a Vermont Farm - Stunning Panoramic Views!
2
1.0
6
Hartland Vermont Cabin
From $605 per night
(USD)
Okemo Hideaway – Secluded Woodland Chalet 7 minutes to Slopes & Village
6
2.0
13
Ludlow Vermont Chalet
From $615 per night
(USD)
Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!
2
1.0
8
Ludlow Vermont Private vacation home
From $594 per night
(USD)
Okemo Mountain Ski in Ski Out Slopeside Vacation Condo
2
2.0
6
Ludlow Vermont Condo
From $328 per night
(USD)
SALE! MUSIC on the Mountain! Come enjoy this cozy, renovated home by Okemo Mtn!
3
2.0
6
Ludlow Vermont Private vacation home
From $310 per night
(USD)
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
1
1.0
4
Windsor Vermont Cabin
From $534 per night
(USD)
Luxury 5-BR Mountain Estate 5-Min to Okemo
5
3.0
12
Ludlow Vermont Private vacation home
From $912 per night
(USD)
Beautiful Historic Country Estate – Modern Comfort in Okemo Valley
5
3.0
10
Cavendish Vermont Private vacation home
From $695 per night
(USD)
OKEMO SKI IN-OUT. Walk to Pool,Hottubs,bar,free e-car charger
2
2.0
8
Ludlow Vermont Condo
From $1153 per night
(USD)
Luxe VT Leaf-Peeping Retreat near Historic Rte 100
4
3.0
11
Weston Vermont Private vacation home
From $465 per night
(USD)
1 Mi to Okemo Mtn Resort: Ludlow Home w/ Hot Tub
3
3.0
8
Ludlow Vermont Private vacation home
From $1205 per night
(USD)
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
5
4.0
14
Ludlow Vermont Chalet
From $805 per night
(USD)
11 BR, 7 Bth, 1/2 mile to Okemo, Hot Tub, on Ski Shuttle, King Bed, Walk to Town
11
7.0
32
Ludlow Vermont Lodge
From $1410 per night
(USD)
The Red Bridge House. 360° of lake views.
3
2.0
9
Ludlow Vermont Private vacation home
From $603 per night
(USD)
Killington Cabin, Hot Tub & Foliage Views!
3
2.0
8
Stockbridge Vermont Cabin
From $491 per night
(USD)
Beautiful Vacation Home with Spectacular Views
2
2.0
4
Hartford Vermont Private vacation home
From $678 per night
(USD)
Historic 1840's Home with large deck, outdoor living room & fire pit. Sleeps 19!
7
5.0
19
Plymouth Vermont Private vacation home
From $954 per night
(USD)
Woodstock Village Green Location, Walk Everywhere, River Patio, Covered Bridge
4
2.0
8
Woodstock Vermont Private vacation home
From $1339 per night
(USD)
Log Cabin home with Mt Ascutney views and pool table
4
4.0
14
Brownsville Vermont Cabin
From $521 per night
(USD)
Killington, Left Side of Duplex ,Outside Hot Tub, Charming, Cozy, Clean
4
1.0
10
Killington, West Bridgewater Vermont Private vacation home
From $668 per night
(USD)
Savage Hart Farm Is A Small Sheep Farm With Guest Accommodations.
1
1.0
4
Hartford Vermont Apartment
From $320 per night
(USD)
Mountain Top Cabin With Incredible Okemo Views And Sunsets
4
2.0
10
Ludlow Vermont Cabin
From $726 per night
(USD)
149 Upper Crossroad Unit B
3
2.0
8
Ludlow Vermont Private vacation home
From $366 per night
(USD)
Classic, cozy farmhouse in the 4 season playground of VT's prettiest town!
4
2.0
8
Woodstock Vermont Private vacation home
From $564 per night
(USD)
Secluded and Serene - GET AWAY FROM IT ALL! Barnard, VT
2
1.0
8
Barnard Vermont Cabin
From $225 per night
(USD)
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
4
2.0
7
Woodstock Vermont Private vacation home
From $613 per night
(USD)
Renovated Luxury 4 Bedroom 3.5 Bath Okemo Trailside
4
2.0
8
Ludlow Vermont Condo
From $1504 per night
(USD)
OKEMO VACATION HOUSE, HOT TUB, CENTRAL AIR 6 Bdrm (2 K, 3 Q, 1 bunk), sleeps 14
6
5.0
14
Ludlow Vermont Private vacation home
From $1086 per night
(USD)
Cozy 2 bedroom minutes from Okemo base lodge - Inquire about seasonal rental
2
1.0
6
Ludlow Vermont Apartment
From $268 per night
(USD)
Quechee: Fantastic Four Bedroom Home Close to Club
4
3.0
8
Hartford Vermont Private vacation home
From $643 per night
(USD)
Charming and Chic Village Rental
1
1.0
4
Woodstock Vermont Apartment
From $387 per night
(USD)
Meadow View- 35 Acres outside your door
1
1.0
4
West Windsor Vermont Private vacation home
From $318 per night
(USD)
The Little Red Cabin! Less than 15 minutes to Okemo! Close to Everything VT!
2
1.0
4
Cavendish Vermont Cabin
From $236 per night
(USD)
Lakefront Vacation House w/ quiet, sandy beach/boats -
4
2.0
10
Plymouth Vermont Private vacation home
From $495 per night
(USD)
Chic Cabin near Killington for Relaxing and Co-working
5
2.0
12
Hartland Vermont Private vacation home
From $950 per night
(USD)
Deluxe Two Bedroom Suite on the 1st floor with outdoor heated pool 10102
2
2.0
8
Killington Vermont Hotel
From $278 per night
(USD)
Scenic South Woodstock, Vermont home
4
2.0
6
South Woodstock Vermont Private vacation home
From $673 per night
(USD)
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
1
1.0
4
Killington Vermont Apartment
From $167 per night
(USD)
Picture-Perfect Vermont Mtn Cabin w/ Hot Tub!
6
3.0
15
Bridgewater Vermont Cabin
From $1059 per night
(USD)
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
3
2.0
6
Cavendish Vermont Condo
From $541 per night
(USD)
Two Double bed Standard Hotel room 218
1
1.0
4
Killington Vermont Hotel
From $141 per night
(USD)
Deluxe Two Bedroom Suite on the 1st floor with outdoor heated pool 10506
1
2.0
8
Killington Vermont Hotel
From $278 per night
(USD)
108 Deluxe One bedroom Queen Suite on the 1st floor w/ outdoor heated pool
1
1.0
4
Killington Vermont Hotel
From $167 per night
(USD)
107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool
1
1.0
4
Killington Vermont Hotel
From $141 per night
(USD)
Warm & inviting 4-bedroom home, open floor plan just steps to Okemo Mtn Resort
4
2.0
12
Ludlow Vermont Private vacation home
From $621 per night
(USD)
Your Year-Round Mountain Escape in Ludlow—Just Minutes from Okemo
3
1.0
8
Ludlow Vermont Private vacation home
From $434 per night
(USD)
Sunset Cabin - your private romantic hideaway
1
1.0
2
West Windsor Vermont Cabin
From $218 per night
(USD)
On Okemo and steps Sachem trail!
3
2.0
8
Ludlow Vermont Private vacation home
From $594 per night
(USD)
Beautiful Log Cabin in Weston, VT
2
2.0
8
Weston Vermont Cabin
From $537 per night
(USD)
Marsh Brook is a beautiful farmhouse located in the heart of the Green Mountains
4
3.0
8
Rochester Vermont Agritourism
From $341 per night
(USD)
Charming & Affordable Home! 1.5 miles from Okemo!
4
2.0
10
Ludlow Vermont Private vacation home
From $437 per night
(USD)
149 upper cross unit A
3
2.0
8
Ludlow Vermont Private vacation home
From $366 per night
(USD)
The Cabin that brings people together
5
3.0
25
Bridgewater Vermont Cabin
From $1045 per night
(USD)
Winter Wonderland At Winterplace K-103!
3
2.0
10
Ludlow Vermont Condo
From $775 per night
(USD)
New Construction 4 season Killington VT Ski House on Lake Amherst okemo
3
2.0
8
Plymouth Vermont Private vacation home
From $361 per night
(USD)
109 Deluxe One bedroom Queen Suite on the 1st floor w/ outdoor heated pool
2
1.0
4
Killington Vermont Hotel
From $167 per night
(USD)
Queen Studio on the 2nd floor with outdoor heated pool 207
1
1.0
4
Killington Vermont Hotel
From $141 per night
(USD)
Deluxe Two Bedroom Suite on the 2nd floor with outdoor heated pool 20304
1
2.0
8
Killington Vermont Hotel
From $278 per night
(USD)
Deluxe One bedroom Queen Suite with outdoor heated pool 203
2
1.0
4
Killington Vermont Hotel
From $147 per night
(USD)
Deluxe One Bedroom Queen Suite on the 2nd floor with outdoor heated pool 202
1
1.0
4
Killington Vermont Hotel
From $146 per night
(USD)
Deluxe 1 bedroom suite located on first floor with outdoor heated pool 118/120
1
2.0
6
Killington Vermont Hotel
From $182 per night
(USD)
Cedarbrook Junior Suite 11416
2
2.0
6
Killington Vermont Hotel
From $182 per night
(USD)
Ski-in /Out. Spacious 2BR / 2.5B Ground-Floor Condo. 4 Seasons of enchantment.
2
2.0
6
Ludlow Vermont Condo
From $677 per night
(USD)
2 Bedroom Condo in Quechee, ~VT~ - a Four Season Community!
2
1.0
6
Quechee Vermont Condo
From $321 per night
(USD)
Peaceful Brookside North Pomfret Cottage
2
1.0
5
Pomfret Vermont Private vacation home
From $332 per night
(USD)
Luxury Ski In Ski Out Okemo Trailside Condo on Sachem Trail -Direct Ski Access
3
2.0
8
Ludlow Vermont Private vacation home
From $1649 per night
(USD)
Modern Farmhouse on 25 Acres / Superb Views.
3
3.0
6
Rochester Vermont Private vacation home
From $669 per night
(USD)
Cozy Historic Hilltop Cottage with Mount Ascutney View
2
1.0
4
West Windsor Vermont Cottage
From $267 per night
(USD)
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