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Leicester Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Leicester vacation rentals

Coffee/tea maker, fridge, microwave, oven

1. Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Leicester
10.0 out of 10, Exceptional, (95 reviews)
"The cottage was just lovely. Very comfortable. And the host was really nice and helpful. A wonderful stay!"
United States
Laura Ann
The price is AED 523
AED 808 total
includes taxes & fees
18 Oct - 19 Oct
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Outdoor dining

2. Glamping hut with WiFi in Ripton, biking, hiking, skiing

Glamping hut with WiFi in Ripton, biking, hiking, skiing
Ripton
9.4 out of 10, Exceptional, (9 reviews)
"Beautiful, magical location, and prompt communication."
United States
Alex
The price is AED 327
AED 839 total
includes taxes & fees
29 Sep - 30 Sep
Glamping hut with WiFi in Ripton, biking, hiking, skiing
Property grounds

3. Lakeside Lodge at Fern Lake: 3BR/1BA Waterfront w/ Dock

Lakeside Lodge at Fern Lake: 3BR/1BA Waterfront w/ Dock
Leicester
10.0 out of 10, Exceptional, (1 review)
"Everything was spectacular! Fern Lake is peaceful and breathtaking. Lake house was wonderful, and amazing. It was spacious, yet homie."
United States
Eric A.
The price is AED 1,248
AED 2,657 total
includes taxes & fees
24 Sep - 25 Sep
Lakeside Lodge at Fern Lake: 3BR/1BA Waterfront w/ Dock
Exterior

4. *Downtown Middlebury Waterfall Studio Apartment*

*Downtown Middlebury Waterfall Studio Apartment*
Middlebury
9.8 out of 10, Exceptional, (10 reviews)
"This is the first review I have ever written. The property and the ownership were fantastic. I found the property to be better than advertised and can’t wait to stay there again. Highly recommended! "
United States
Steve S.
The price is AED 424
AED 1,222 total
includes taxes & fees
30 Sep - 1 Oct
*Downtown Middlebury Waterfall Studio Apartment*
Exterior

5. Robert Frost Mountain Cabins

Robert Frost Mountain Cabins
3.5 star property
Ripton
10.0 out of 10, Exceptional, (42 reviews)
"Very nice place great owner"
United States
Joe
The price is AED 1,113
AED 1,213 total
includes taxes & fees
29 Sep - 30 Sep
Robert Frost Mountain Cabins
Exterior detail

6. Downtown Middlebury 3 BR Home - Walk Everywhere!

Downtown Middlebury 3 BR Home - Walk Everywhere!
Middlebury
9.6 out of 10, Exceptional, (34 reviews)
"Great location, very clean"
United States
Karyn M.
The price is AED 420
AED 1,168 total
includes taxes & fees
28 Sep - 29 Sep
Downtown Middlebury 3 BR Home - Walk Everywhere!
Exterior detail

7. Charming one bedroom just minutes to Middlebury!

Charming one bedroom just minutes to Middlebury!
New Haven
10.0 out of 10, Exceptional, (2 reviews)
"Lovely unit, clean, well equipped, quiet location"
United States
Jane
The price is AED 340
AED 894 total
includes taxes & fees
30 Sep - 1 Oct
Charming one bedroom just minutes to Middlebury!
Interior

8. Gracious two bedroom just minutes to Middlebury!

Gracious two bedroom just minutes to Middlebury!
New Haven
The price is AED 621
AED 1,300 total
includes taxes & fees
28 Sep - 29 Sep
Gracious two bedroom just minutes to Middlebury!
TV, fireplace

9. Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
Killington
9.8 out of 10, Exceptional, (14 reviews)
"We had such a great time staying here. It was clean, cozy and so convenient to walk right out the door to the slopes! "
United States
Susanne B.
The price is AED 482
AED 1,425 total
includes taxes & fees
24 Sep - 25 Sep
Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
Exterior

10. Unique family-friendly Vermont cabin!

Unique family-friendly Vermont cabin!
Fair Haven
10.0 out of 10, Exceptional, (25 reviews)
"Awesome places today stay "
United States
James L.
The price is AED 658
AED 1,088 total
includes taxes & fees
24 Sep - 25 Sep
Unique family-friendly Vermont cabin!
Interior

11. Ski Home/Arcade Mountain Views Near Killington/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
United States
Kevin M.
The price is AED 489
AED 2,141 total
includes taxes & fees
24 Sep - 25 Sep
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Exterior

12. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
The price is AED 391
AED 2,019 total
includes taxes & fees
24 Sep - 25 Sep
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Exterior

13. Inviting timber frame cabin in Vermont's Green Mountains

Inviting timber frame cabin in Vermont's Green Mountains
Ripton
10.0 out of 10, Exceptional, (7 reviews)
"Welcoming, charming, and very clean cabin with excellent communication with team and fun access to trails, hot tub and game room."
United States
Kelly I.
The price is AED 1,222
AED 1,621 total
includes taxes & fees
27 Sep - 28 Sep
Inviting timber frame cabin in Vermont's Green Mountains
Smart TV, fireplace, DVD player, books

14. Charming and meticulously cleaned cabin with panoramic view of the Green Mtns

Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
Ripton
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful place. Lots to do around the cabin and in the area. The hosts are very helpful. The cabin has everything you could want for a great stay. "
United States
Susan
The price is AED 1,107
AED 1,487 total
includes taxes & fees
29 Sep - 30 Sep
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
Exterior

15. Cozy and pristine timberframe cabin

Cozy and pristine timberframe cabin
Ripton
10.0 out of 10, Exceptional, (4 reviews)
"It is a gorgeous property with lots of fun amenities...perfect for a winter getaway"
United States
Karen H.
The price is AED 1,107
AED 1,479 total
includes taxes & fees
24 Sep - 25 Sep
Cozy and pristine timberframe cabin
Outdoor dining

16. Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub

Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub
North Sherburne
8.2 out of 10, Very good, (14 reviews)
"We had a great time!"
United States
Matthew R.
The price is AED 559
AED 1,669 total
includes taxes & fees
24 Sep - 25 Sep
Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub
1 bedroom, desk, iron/ironing board, travel crib

17. Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Killington
10.0 out of 10, Exceptional, (17 reviews)
"Great condo and building. Everything in excellent condition. Convenient location."
United States
Joseph S.
The price is AED 463
AED 1,000 total
includes taxes & fees
24 Sep - 25 Sep
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Interior

18. Tasteful two bedroom just minutes to Middlebury!

Tasteful two bedroom just minutes to Middlebury!
New Haven
The price is AED 569
AED 1,250 total
includes taxes & fees
24 Sep - 25 Sep
Tasteful two bedroom just minutes to Middlebury!
Exterior

19. Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.8 out of 10, Exceptional, (27 reviews)
"We had a great time! "
United States
Allie T.
Beautiful home located in the Mad River Valley
1 bedroom, desk, WiFi (free), bed sheets

20. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (16 reviews)
"The location was perfect, the property is very well maintained and comfortable. I would highly recommend this place!"
United States
Valerie
The price is AED 364
AED 719 total
includes taxes & fees
29 Sep - 30 Sep
Cozy Rutland Retreat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Leicester Hotel Reviews

Circle Court Motel

Circle Court Motel

8/10 Good
"Huge thank you; the staff was so helpful with information and guidance on where to eat and how to navigate the town. Just a few items worth mentioning: it's a basic room, no fancy fixtures. The lamp between the two queen-size beds didn't work, which wasn't a problem because of the overhead light. Some items need updating. But overall, our goal was just a place to sleep, and it was comfortable; the sheets were soft, and we had a good night's sleep- nice and quiet! Would recommend and would definitely stay there again."
Gladys 1-night trip
Posted 4 hours ago
Circle Court Motel

Frequently asked questions

Are there vacation rentals in Leicester?

Yes, we give you a choice of vacation rentals close to popular local attractions in Leicester, or you can select a more secluded option if you want a relaxing place to stay.

What can I see and do in Leicester?

Explore the area and family-friendly sights such as Hathaway Farm, or get out into nature at a spot like Lake Dunmore. In the larger area, you’ll find Leicester Town Hall and Branbury State Park.

What are vacation rentals like in Leicester?

Vacation rentals are privately owned properties you can stay in for a couple days or more in Leicester. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for families.