Holiday Rentals Rutland from £126: Find Short-Term Rentals & Holiday Accommodations

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Our top choices for Rutland holiday rentals

A modern kitchen with a dishwasher, a coffee maker, and a dining area with a wooden table set for two.

1. Cozy Rutland Retreat

Rutland

Susan E.

includes taxes & fees

23 Nov - 24 Nov

A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

2. new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

Mendon

Aurore H.

includes taxes & fees

9 Nov - 10 Nov

A house with a wooden deck, solar panels, and a well-maintained garden.

3. Kingsley Homestead - 2 Bedroom retreat

Rutland

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with stainless steel appliances, wooden flooring, and white cabinetry.

4. Rutland apartment on the bus route with central A/C, near Pico

Rutland

Thomas A.

includes taxes & fees

9 Nov - 10 Nov

A kitchen with granite countertops, wooden cabinets, and a built-in oven.

5. The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

Mendon

Diane

includes taxes & fees

8 Nov - 9 Nov

A house with a covered deck, a barbecue grill, and a wooden pergola.

6. large ski ranch hot tub close to killington pets ok

Mendon

Callison A.

includes taxes & fees

15 Nov - 16 Nov

A dining area with a wooden table, four chairs, a coffee maker, and a trash can.

7. Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort

Chittenden

"Loved this stay - the farmhouse is authentic and oozes charm! Everything about this stay was easy - 20min drive to the slopes, 15 min to downtown Rutland, and an extremely well-equipped house to easily accommodate the six of us. Superb communication from the host both prior to and during our stay (promptly answered several questions for us). If you want a vintage farmhouse feel as opposed to a modern condo-style stay, this is the place for you!"

Carl P.

includes taxes & fees

12 Nov - 13 Nov

A rustic cabin with a stone fire pit, wooden deck, and a chimney.

8. Forest Mountain Ski Retreat. 20 min to Killington/14 to Pico.

Mendon

Heidi S.

includes taxes & fees

8 Nov - 9 Nov

A modern kitchen with a large island, white cabinetry, and a stainless steel refrigerator.

9. Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.

Rutland

Matthew T.

includes taxes & fees

8 Nov - 9 Nov

A modern kitchen with white cabinets, stainless steel appliances, a window with a view, and a 'GATHER' sign above the window.

10. Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Rutland

includes taxes & fees

11 Nov - 12 Nov

A hallway with a wooden wall, a white door, and a wooden staircase.

11. 4BR Home | Walk Downtown Rutland + Trails

Rutland

Dominic C.

includes taxes & fees

11 Nov - 12 Nov

A swimming pool with a hot tub, surrounded by a building with balconies and a fenced area with trees.

12. Mountain Green ground-floor condo with private yard off the patio

Killington

includes taxes & fees

12 Nov - 13 Nov

A modern bedroom with a bed, bedside table, and a window with a view.

13. The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

Killington

Nathan H.

includes taxes & fees

8 Nov - 9 Nov

A yurt with a red door, a visible interior with a fire, and snow outside.

14. Off-Grid Mongolian Yurt on Vermont Sheep Farm

Poultney

includes taxes & fees

9 Nov - 10 Nov

A modern living room with a glass coffee table, a sofa, a TV mounted on the wall, a fireplace, and a blue accent wall.

15. Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Killington

Carla M.

includes taxes & fees

8 Nov - 9 Nov

An aerial view of a residential area with houses, a swimming pool, and a parking lot.

16. Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Killington

Asad B.

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with stainless steel appliances, a dining area with a glass table, and a living room with a fireplace.

17. Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.

Killington

Riley T.

A ski resort with multiple buildings, a ski slope, and a mountain in the background.

18. Jack S`Bearo - Slopes, Fireplace, Pool

Killington

Joseph S.

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with a central island, stainless steel appliances, and wooden cabinets.

19. Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

Killington

Spencer P.

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with a microwave, stove, and red stools. A living area with a fireplace and a TV is visible in the background.

20. Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332

Killington

John O.

includes taxes & fees

8 Nov - 9 Nov

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Find holiday rentals that suit your style

Top Rutland Hotel Reviews

A covered outdoor deck with wicker furniture, a table, and a built-in grill.

Mountain Meadows Lodge

Killington

10/10 Excellent

Andrew

A modern kitchen with a central island, stainless steel appliances, and a dining area with chairs.

Sleep Woodstock Motel

Woodstock

8/10 Good

I always thought motels were rather unpleasant and distasteful - well, I could not have been any more mistaken! My partner and I absolutely loved this motel; it was conveniently located, the surroundings were gorgeous and our room was one you would expect to find in a proper nice hotel. It was clean, modern, had a big flat-screen TV and the bed was super comfortable! The level of attention upon arrival and throughout the whole stay was also flawless. We were greeted by Patrick, who is the...

Angel

A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

Fat Sheep Farm & Cabins

Windsor

10/10 Excellent

This was a wonderful one night stay as part of our leaf peeping trip to Vermont from the UK. One thing to be aware of is that GPS/satnav is really bad in this area. Make sure you take printed written instructions of how to find them. The cabin is absolutely lovely. It’s really well equipped, especially the kitchen which has good quality knives, saucepans, frying pans, etc important if you’re going to be doing your own cooking. Lovely little touches of leaving a couple of home-made scones and...

David

A modern interior with a wooden reception desk, seating area, and large windows.

Hampton Inn Rutland

Rutland

10/10 Excellent

John

A lakeside setting with a stone fire pit surrounded by logs, a grassy area, and a building with outdoor seating in the background.

Lake Bomoseen Lodge

Bomoseen

10/10 Excellent

David

A hotel entrance with three illuminated arches and a flag.

The Lilac Inn

Brandon

10/10 Excellent

Rosina

A spacious living room with a high ceiling, wooden beams, a staircase, and a large window.

Greenbrier Inn

Killington

10/10 Excellent

Scott

A two-story building with a bar and restaurant on the ground floor, a vintage car parked in front, and a sign indicating "Main Mountain".

Main and Mountain Bar & Motel

Ludlow

10/10 Excellent

Justin

A spacious indoor area with a large dining table, several chairs, and a sofa. There is a glass door leading outside, and the room has a wooden ceiling structure.

Best Western Inn & Suites Rutland-Killington

Rutland

10/10 Excellent

Marion

A stone fireplace with a sign above it reading "Trailside Lodge."

The Trailside Inn

North Sherburne

10/10 Excellent

Daniel

Find out more about Rutland

Everything you need to know about Rutland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Rutland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Rutland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Rutland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Rutland. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Rutland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Rutland holiday rentals we have selected for you start as low as £126 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Rutland rentals

At Expedia, we put the best Rutland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Rutland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Rutland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Rutland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find a holiday rental in Rutland?

Yes, there are holiday rentals in Rutland close to Vermont State Fairgrounds, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Rutland speak highly of the ski slopes and array of shops. Make sure to also enjoy the majestic mountain landscape and top-notch restaurants during your holiday.

What are some of the best holiday rentals that Rutland has to offer?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This holiday home rental outside of Rutland is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Rutland?

Choose from 56 Expedia holiday rentals in Rutland for a memorable holiday.

What can I see and do in Rutland?

Cultural attractions include Paramount Theater and Chaffee Art Center, whereas Pine Hill Park and Green Mountain National Forest are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Vermont State Fairgrounds and Killington Resort.

What are holiday rentals like in Rutland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Rutland. Holiday rentals offer extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a small group gathering.

Search Holiday Rentals in Rutland

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Rutland holiday rentals

1. Cozy Rutland Retreat

2. new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

3. Kingsley Homestead - 2 Bedroom retreat

4. Rutland apartment on the bus route with central A/C, near Pico

5. The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

6. large ski ranch hot tub close to killington pets ok

7. Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort

8. Forest Mountain Ski Retreat. 20 min to Killington/14 to Pico.

9. Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.

10. Relaxing Rutland Retreat Near Skiing, Dining & Hiking

11. 4BR Home | Walk Downtown Rutland + Trails

12. Mountain Green ground-floor condo with private yard off the patio

13. The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

14. Off-Grid Mongolian Yurt on Vermont Sheep Farm

15. Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

16. Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

17. Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.

18. Jack S`Bearo - Slopes, Fireplace, Pool

19. Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

20. Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332

Find holiday rentals that suit your style

Top Rutland Hotel Reviews

Mountain Meadows Lodge

10/10 Excellent

Find out more about Rutland

Rutland holiday rentals: An excellent choice for every season

How to find incredible deals on Rutland rentals

Frequently Asked Questions

Can I find a holiday rental in Rutland?

What are some of the best holiday rentals that Rutland has to offer?

How many holiday rentals are there in Rutland?

What can I see and do in Rutland?

What are holiday rentals like in Rutland?

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