Leicester Vacation Rentals

Q: What are some of the best vacation home rentals that Leicester has to offer?

Water front home with large two tiered deck! 2 bathrooms 😂 : You might want to consider this vacation home rental near Leicester, which is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

Dates

November 2026

December 2026

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Our top choices for Leicester vacation rentals

A kitchen with a large island, wooden ceiling beams, and various kitchen appliances.

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

Leicester

Laura Ann

AED 724 total

includes taxes & fees

22 Nov - 23 Nov

A snow-covered house with a lit entrance and a small outdoor light feature.

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

Ripton

Alex

AED 798 total

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with white cabinets, a coffee machine, and a wooden accent wall.

3. Charming one bedroom just minutes to Middlebury!

New Haven

Jane

AED 804 total

includes taxes & fees

10 Nov - 11 Nov

A room with a large window overlooking a forest in autumn.

4. Beautiful home located in the Mad River Valley

Warren

Lyra F.

AED 1,030 total

includes taxes & fees

2 Dec - 3 Dec

A large grassy field with a historic building in the background.

5. Purple Door Cottage in the heart of Middlebury!

Middlebury

carol m.

AED 1,358 total

includes taxes & fees

10 Nov - 11 Nov

A modern living room with a sofa, coffee table, and a dining area with chairs and a table.

6. Tasteful two bedroom just minutes to Middlebury!

New Haven

AED 1,105 total

includes taxes & fees

10 Nov - 11 Nov

A rustic cabin surrounded by autumn foliage.

7. Beautiful home located in the Mad River Valley

Warren

Sloan S.

AED 884 total

includes taxes & fees

11 Nov - 12 Nov

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

8. Cozy Rutland Retreat

Rutland

Susan E.

AED 671 total

includes taxes & fees

23 Nov - 24 Nov

A modern kitchen with stainless steel appliances, a granite countertop, and pendant lighting.

9. Gracious two bedroom just minutes to Middlebury!

New Haven

AED 1,145 total

includes taxes & fees

10 Nov - 11 Nov

10. Beautiful home located in the Mad River Valley

Warren

Allie T.

AED 884 total

includes taxes & fees

11 Nov - 12 Nov

A red barn in a forested area with mountains in the background.

11. Charming Barn Carriage House in Green Mountains of Vermont Near Middlebury

Ripton

Lani C.

AED 1,016 total

includes taxes & fees

28 Nov - 29 Nov

A wooden staircase leading to a covered outdoor area with a view of a green lawn and trees.

12. Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around

Hancock

Kevin J.

AED 1,712 total

includes taxes & fees

16 Nov - 17 Nov

A log cabin interior with a kitchen, dining area, and a large window.

13. Quintessential Vermont Log Chalet • Fire Pit • Private Deck • Sugarbush

East Warren

Beth Y.

AED 1,321 total

includes taxes & fees

1 Dec - 2 Dec

A wooden shed with a cross-braced door in a garden with a house in the background.

14. Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings

North Sherburne

Matthew R.

AED 1,413 total

includes taxes & fees

10 Nov - 11 Nov

A spacious living area with a wooden ceiling, a sofa, a chair, a television, and a staircase.

15. Delightful 2-bedroom, solar-powered cabin in charming Vermont awaits you

Chittenden

AED 1,316 total

includes taxes & fees

10 Nov - 11 Nov

A wooden table with a bottle of wine, glasses, and grapes.

16. Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest

Ripton

Steven

AED 1,232 total

includes taxes & fees

10 Nov - 11 Nov

A wooden cabin with a snow-covered roof, a porch with a green door, and a small window on the side.

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

Ripton

Kelly I.

AED 1,175 total

includes taxes & fees

15 Nov - 16 Nov

A cozy living room with a wooden ceiling, a fireplace, a television, and a comfortable seating area.

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

Ripton

Susan

AED 1,232 total

includes taxes & fees

10 Nov - 11 Nov

A bedroom with a large bed, a TV mounted on the wall, and a sliding door leading to a bathroom.

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

Killington

Joseph S.

AED 986 total

includes taxes & fees

10 Nov - 11 Nov

A spacious loft with a high ceiling, a cozy living area with a brown sofa and a coffee table, a kitchen with wooden cabinets, and a dining area with a table and chairs.

20. Sunny Alpine Suite • Walk to Lake • Private Deck • Yard and Gardens w/Fire Pit

East Warren

Laura H.

AED 1,078 total

includes taxes & fees

12 Nov - 13 Nov

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Find vacation rentals that suit your style

Top Leicester Hotel Reviews

Brandon Inn

Brandon

10/10 Excellent

Shahram

A two-story house with a porch, surrounded by trees.

Inn at Neshobe River

Brandon

10/10 Excellent

Anonymous traveler

A grocery store aisle with candy dispensers and bulk bins.

Middlebury Sweets Motel

Middlebury

10/10 Excellent

I booked at this motel at the last minute and was very apprehensive because I usually don’t stay in motel. It, since my last minute stay was for one night and the reviews were good, I said ‘hey’ why not. I’m only going to stay overnight! Needless, to say the good reviews this place received were right on point. I was truly surprised by the courtesy and efficiency of this small family owned motel. Room was cleaned and had absolutely everything needed. The candy store couple doors down & candy...

Edith

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

Anonymous traveler

A white building with green shutters and a sign that reads "Storeham Inn."

Shoreham Inn

Shoreham

10/10 Excellent

Nice inn located in a 200 year old house. Rooms with comfortable beds, no tv, but they do have WiFi. Food is very good and the couple that owns and runs the inn is very friendly and accommodating. Some quirks like squeaky floors and no locks on the doors just add to the charm. Nice fireplace and outdoor deck. Coffee is excellent too. Very nice place to stay you have something going on in the area, or if you want a relaxing low key vacation in picturesque Vermont or nearby upstate NY.

Ron

A large, two-story house with a driveway leading to a garage, surrounded by a well-maintained lawn and autumn-colored trees.

The Lilac Inn

Brandon

10/10 Excellent

Karen

A large, multi-story hotel with a covered entrance and multiple windows.

Courtyard Middlebury

Middlebury

10/10 Excellent

Shawn

A spacious living room with a stone fireplace, wooden furniture, and a large potted plant.

The Trailside Inn

North Sherburne

10/10 Excellent

I've never wrote a review on any product or hotel until now and that is because the Trailside Inn deserves all the recognition it could get! To start, the owners Josh and Ann are fantastic. We arrived Friday night after a long drive from Long Island - we were immediately greeted by Josh who welcomed us to the lodge and took the time to show us the best trails at Killington and offered advice on restaurants near by. It was very cold Saturday so we didn't stay long at the mountain. When we...

Alyssa

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

Judie

A spacious room with large windows, a stone wall, and a wooden ceiling.

The Mountain Top Inn & Resort

Chittenden

10/10 Excellent

We only stayed for two nights but could not have been happier! The staff was extremely helpful and friendly. The views and grounds are beautiful. We loved the beautiful, quiet setting. It rained one of the days we were at the hotel, but the staff was eager to give recommendations of places to go for other indoor activities! We were extremely pleased to visit the Mountain Top Inn and will definitely return for another stay!

Anonymous traveler

A large, modern house with a prominent wooden structure and stone foundation.

Best Western Plus Ticonderoga Inn & Suites

Ticonderoga

10/10 Excellent

Anonymous traveler

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 are some of the best vacation home rentals that Leicester has to offer?

Water front home with large two tiered deck! 2 bathrooms 😂: You might want to consider this vacation home rental near Leicester, which is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.

Leicester Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Leicester vacation rentals

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

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

3. Charming one bedroom just minutes to Middlebury!

4. Beautiful home located in the Mad River Valley

5. Purple Door Cottage in the heart of Middlebury!

6. Tasteful two bedroom just minutes to Middlebury!

7. Beautiful home located in the Mad River Valley

8. Cozy Rutland Retreat

9. Gracious two bedroom just minutes to Middlebury!

10. Beautiful home located in the Mad River Valley

11. Charming Barn Carriage House in Green Mountains of Vermont Near Middlebury

12. Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around

13. Quintessential Vermont Log Chalet • Fire Pit • Private Deck • Sugarbush

14. Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings

15. Delightful 2-bedroom, solar-powered cabin in charming Vermont awaits you

16. Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest

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

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

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

20. Sunny Alpine Suite • Walk to Lake • Private Deck • Yard and Gardens w/Fire Pit

Find vacation rentals that suit your style

Top Leicester Hotel Reviews

Brandon Inn

10/10 Excellent

Frequently Asked Questions

Are there vacation rentals in Leicester?

What are some of the best vacation home rentals that Leicester has to offer?

What can I see and do in Leicester?

What are vacation rentals like in Leicester?