
House holiday rentals in Rutland
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Top-rated house rentals in Rutland
Guests agree: these houses are highly rated for location, cleanliness and more.

Quechee Haus: hot tub, sauna, & mountain views
Hathaway House: an 1850s barn perched atop a hill remade into a stunning modern farmhouse w/ Green Mountain views west, hot tub, sauna, chef's kitchen, separate study, & fiber internet. Play games on the huge lawn, or ping pong & foosball in barn game room. Enjoy the gardens or dinner by the fire. Grill & eat al fresco on the huge deck with hot tub, cold plunge. This private retreat is surrounded by nature yet 5 min to Quechee, 15 to Hanover, Woodstock, Lebanon; 35 to Killington & Lake Sunpee.

The Bluebird Day Chalet 2 bed dtwn Ludlow Village
Cozy heart of Ludlow Village location on the shuttle route (free!) for Okemo & close to Echo Lake that sleeps 6. As downtown as possible! Okemo shuttle stop at The Mill. Quick walk to good eats & drinks (Downtown Grocery, Stemwinder, Main + Mountain, etc.), Shaws, Rite Aid, and The Wine & Cheese Shop (perfect for après ski!). On site parking for 2 cars & free on street parking if needed (no overnight). Wifi & smartTV to stream your favorites while you relax after a long day on the slopes.

Beautiful Woodstock Home-Perfect for entertaining
Newly renovated - 4 bedroom, 3 bath house, perfect for relaxing or entertaining. Close to all that the Woodstock Village and the Upper Valley has to offer. Amazing location! Only 1.5 mi to the Woodstock Green. Explore the property and feast on the blackberries in summer, raid the tomato garden in the late summer/early fall, and pick the wild fall apples for munching or baking. Bring your snowshoes or cross country skis (in winter) or hiking shoes in summer and explore the property and beyond!

The Oaks - secluded rural estate w/ amazing views
Relax in this private house secluded off a 1,000-ft driveway in the hills of NH overlooking Mt. Ascutney and the Connecticut River valley. This is the 45-acre estate known as "The Oaks" previously owned by painter Maxfield Parrish. Huge oak trees and rocky ledges abound. Great for gatherings with family or friends. Close to Dartmouth College, Woodstock, and ski areas - or just sit on the porch and take in the views. Weddings and reunions can be hosted (tent rentals and catering by others).

Stunning Okemo Views - 3BD 3BA on 10 Private Acres
Recently constructed on ten private acres with captivating views of Okemo. Three BR, three full bath, air conditioned modern chalet, just 1.5 miles from downtown and 3 miles from Okemo’s base areas. Epic views of Okemo and surrounding mountains from every room. Cozy around the fireplace in the living room or enjoy smores outside by the firepit, or unwind on the deck. Lower level has second living room great for kids with large TV, comfy couches, Pac Man arcade, foosball and board games.

Charming, Cozy Cape
Enjoy the warmth, style, and privacy of this lovely home, located on a hillside above the picturesque White River. Just minutes from restaurants, shopping, cocktail bars, and galleries in downtown White River Junction, and a 10-minute drive to Hanover, NH, and the Dartmouth College campus. Set on an acre of open land with beautiful views and sunsets from the back deck. Central heating to keep you cozy during the fall and winter months. Perfect for couples and families ... and pet-friendly!

Fresh Snow- Luxury Cabin near Ski Areas
On a cold winter morning Wake up in a luxurious bed in a stylish cabin with panoramic Vermont views. Hot coffee mug warming your hand, step out to the porch, look at faraway hills. Snowshoe/slide/talk/play with your favorite people/animals. Or jump in your car to Okemo/Magic Montain/Killington for a day on the slopes. Take a scenic drive to Woodstock, Simon Pearce, Okemo, or the Harpooon Brewery. Kick back with a night around the firepit stargazing Our Red House welcomes you.

Birdie's Nest Guesthouse
Welcome to our newly renovated studio apartment, nestled among the trees in the serene hills of West Windsor, Vermont. Elevated on the second floor, this separate structure offers a tranquil escape with breathtaking views of Mount Ascutney and our own private pond. Immerse yourself in the comforts of this thoughtfully designed studio apartment, surrounded by the natural beauty of the Vermont landscape. Every detail has been curated to ensure your utmost comfort and enjoyment.

Meadow View. 35 acres outside your door!
Meadow View - pet friendly home away from home. 35 acres- including 2 trout ponds and 25 acres of wooded trails (perfect for hiking, cross country skiing/snow shoeing!). Featuring a newly remodeled kitchen and bathroom. Minutes from Mt. Ascutney (trails galore, rope tow in the winter). The unit is perfect spot for couples craving time in rural Vermont or for families/outdoor enthusiasts who want to go mountain biking, skiing, hiking. (Okemo 30 min Killington 45 min)

Killington Retreat | Deck-Fire Pit-Mountain Views!
Welcome to your new Vermont escape! This custom-built 2BR/1BA pet and smoke free home is nestled in the foothills of the green mountains. Our home sits on a 14 acre lot and is close to hiking, skiing, a horse farm, lakes and Rutland (10 mins). You will love the woodwork, luxury white bedding, floor-to-ceiling windows, massive sunny deck, and peace and quiet. There is plenty of space for family memory making, your peaceful mountain retreat awaits!

Beautiful Historic 1909 Library with a Fireplace
An intimate experience with history! Quechee’s first Library (1909) original hardwood floors and shelves with treasures. Romantic Gas Fireplace, Claw foot tub (with NO shower) in the bedroom, Living area, Kitchenette, AC, WIFI, Comfy Queen bed, Window Seat, unique art, many amenities. Across the street, Covered Bridge, Waterfall, Simon Pearce Restaurant w/ Glass Blowing. Parker House with WhistlePig whiskey tasting and more. Hope you love it!

Private apartment in-town Hanover and near DHMC
Enjoy easy access to everything from this perfectly located home base. Your apartment has a private entrance and is a quick walk to Dartmouth, the shops and restaurants of Hanover, and the Coop supermarket. 5-minute drive to Dartmouth-Hitchcock Memorial Hospital. Kitchenette with mini-fridge, toaster oven, microwave, kettle, single burner plug-in cooktop. Bedroom has queen-size bed. Queen-size pull-out couch in living space. No car needed
Popular amenities for house rentals in Rutland
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington

Ski Back to Trail Creek!

Ranch at Mendon Mt Orchards

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Dana Road House Sunlit VT Country Home w/HotTub

Premier Quechee Newton Village Condo: Pet Friendly

Private Farmhouse with in ground pool!

Historic Home on 17 acres of land. Go escape!
Weekly house rentals

Peaceful Country Getaway 5 Miles from Woodstock VT

Quaint Cottage

Cornish-Windsor Bridge Retreat with Amazing Views

Quechee Vermont Home

Fabulous Log Home in the Woods

Sunflower Burrow Cottage

Elm Gate Farm

Cozy Quechee cabin.
Private house rentals

Killington - Woodstock: Private Oasis w/ Hot-Tub

Beautiful Village of Woodstock home near the Inn

Killington Chalet: Hot Tub, Fireplace, spacious 4b

Cheerful, Restored 1940s Cape- 5 mins to Woodstock

The Cornish Cottage

Secluded Getaway, VT - 15 min from Woodstock

Scandinavian Serenity Close to Okemo

Topridge Ski-on/Ski-off | 4BR w Game Room!
When is the best time to visit Rutland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £316 | £271 | £333 | £206 | £294 | £263 | £290 | £293 | £287 | £259 | £246 | £346 |
| Avg. temp | -5°C | -4°C | 1°C | 7°C | 14°C | 19°C | 22°C | 21°C | 16°C | 10°C | 4°C | -2°C |
Quick stats about house rentals in Rutland

Total holiday rentals
Explore 40 holiday rentals in Rutland

Nightly prices starting at
Rutland holiday rentals start at £111 per night before taxes and fees

Verified guest reviews
Over 1,640 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Rutland holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Rutland rentals

4.9 Average rating
Rutland stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with a patio Rutland
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- Family-friendly rentals Rutland
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- Rentals with a fireplace Rutland
- Pet-friendly rentals Rutland
- Rentals with a firepit Rutland
- House rentals Windsor County
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- House rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Squam Lake
- Sugarbush Resort
- Killington Resort
- Pats Peak Ski Area
- Monadnock State Park
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Weirs Beach
- Pico Mountain Ski Resort
- Tenney Mountain Resort
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Crotched Mountain Ski and Ride
- Montshire Museum of Science
- Ice Castles
- Mount Sunapee Resort
- Dartmouth College
- Squam Lakes Natural Science Center
- Stinson Lake




