A wooden covered bridge in a lush green landscape.

Springfield Vacation Rentals

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Dates

November 2026

December 2026

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Our top choices for Springfield vacation rentals

A two-story house with a deck, surrounded by dense forest.

1. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

Chester

pauline

￥150,620 total

includes taxes & fees

Nov 12 - Nov 13

A red house with a covered porch and a chimney.

2. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Grafton

Neil S.

￥57,162 total

includes taxes & fees

Nov 12 - Nov 13

A staircase with wooden steps and white railings, leading to an upper floor.

3. Explore the upper valley from this spacious Claremont Home

Claremont

Michael R.

￥55,376 total

includes taxes & fees

Nov 13 - Nov 14

4. Charming Chester Farmhouse near Near VT Slopes

Chester Depot

Kimberly B.

￥59,639 total

includes taxes & fees

Nov 22 - Nov 23

A covered porch with wicker furniture, a table, and chairs.

5. Renovated Vermont Retreat with mountain views near Okemo & Killington for 6

Cavendish

Mark G.

￥79,565 total

includes taxes & fees

Nov 18 - Nov 19

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

6. Fat Sheep Farm & Cabins

Windsor

Brenda

￥28,003 total

includes taxes & fees

Nov 30 - Dec 1

A cabin interior with a wooden staircase, a kitchen with modern appliances, and large windows offering a forest view.

7. Cozy Resort Cabin! Hot-Tub Sauna Fire Pit Trails

Cavendish

Joe C.

￥64,158 total

includes taxes & fees

Nov 17 - Nov 18

A rectangular pool with a glass enclosure, surrounded by lounge chairs and umbrellas, set in a landscaped area with trees.

8. Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Cavendish

Ania H.

￥77,867 total

includes taxes & fees

Nov 15 - Nov 16

A spacious living room with a high ceiling, wooden beams, a fireplace, and large windows.

9. Game Room, Fire Pit & Views! Spacious Ludlow Home

Ludlow

￥124,997 total

includes taxes & fees

Nov 15 - Nov 16

A modern kitchen with stainless steel appliances, a wooden dining table set for four, and a seating area with a sofa and chairs.

10. Cozy Village Condo-Okemo Shuttle

Ludlow

walter s.

￥39,637 total

includes taxes & fees

Nov 12 - Nov 13

A residential property with a swimming pool, a covered patio, and a detached garage.

11. 3 BR Luxury Condo at Castle Hill - 5 mi to Okemo

Cavendish

￥96,352 total

includes taxes & fees

Nov 12 - Nov 13

A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

12. Lakefront Family Fun Retreat

Newport

sean c.

￥63,699 total

includes taxes & fees

Nov 13 - Nov 14

A cozy cabin interior with a wooden ceiling, a sofa, a red armchair, a small table with magazines, and a window with curtains.

13. Cozy Vermont Cabin at Trail End Ranch! The Best of VT is all around you!

Andover

Betsy S.

￥66,895 total

includes taxes & fees

Nov 12 - Nov 13

A cozy living room with a fireplace, a black leather sofa, and a television mounted above it.

14. Village Fireplace Shuttle Boot Warmers

Ludlow

Justin P.

￥66,600 total

includes taxes & fees

Nov 30 - Dec 1

A living room with a sofa, a bench, a fireplace, a TV, and a large window.

15. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

Clock Tower Base Area

tiliger01

￥36,713 total

includes taxes & fees

Nov 14 - Nov 15

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

16. Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Ludlow

Tina l.

￥77,771 total

includes taxes & fees

Nov 17 - Nov 18

A living room with a sofa, a coffee table, and a wooden side table. There are two windows with blue frames and a painting on the wall.

17. 3BR/2BA Near Okemo | Vermont Mountain Getaway

Ludlow

￥94,007 total

includes taxes & fees

Nov 18 - Nov 19

A golf course with a winding path, trees, and a hilly landscape.

18. First-floor downtown studio near dining and gear shops, under a mile to Okemo

Ludlow

Brian

￥49,498 total

includes taxes & fees

Nov 13 - Nov 14

A cozy living room with a stone fireplace, large windows, and a wooden ceiling.

19. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Andover

Lorraine C.

￥106,006 total

includes taxes & fees

Nov 12 - Nov 13

A two-story house with a covered porch, a staircase, and a front door with a wreath.

20. First-floor downtown condo, less than a mile from Okemo Mountain

Ludlow

Darcie L.

￥50,962 total

includes taxes & fees

Nov 13 - Nov 14

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Find vacation rentals that suit your style

Top Springfield Hotel Reviews

A hotel with a covered entrance, stone facade, and a sign indicating it is part of the Best Western chain.

Best Western Springfield Hotel

Springfield

10/10 Excellent

JULIA

A cozy living room with a fireplace, leather furniture, and a coffee table with a puzzle.

The Common Man Inn & Restaurant

Claremont

10/10 Excellent

Robert

A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

Harvest Barn Inn

Bellows Falls

10/10 Excellent

Virginia

A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

Stone Hearth Inn and Eatery

Chester

10/10 Excellent

William

A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.

Pointe at Castle Hill Resort

Cavendish

10/10 Excellent

This is the second time we've stayed in a Suite room. King sized bed in the BR; kitchen with full-sized appliances, LR with pull-out Queen sofa, gas fireplace, bathroom with jetted tub! Very comfortable and fully equipped. Small things were so helpful - like doormats for dirty boots, a bench for putting on boots, a closet for skis, complementary packages of New England coffee, Aveda products in the bathroom, kitchen supplies like dish soap, dishwasher detergent, sponge, towels. Then larger...

Marion

A well-maintained garden with a variety of plants and flowers, a wooden pergola, and a gravel path.

Fullerton Inn

Chester Depot

10/10 Excellent

Catherine

A stone fire pit with chairs around it, set in a grassy area with trees and a large building in the background.

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Brownsville

10/10 Excellent

Jamie

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

Anonymous traveler

A spacious living room with a chandelier, multiple armchairs, a coffee table, and a rug.

On The River Inn

West Woodstock

10/10 Excellent

Ayleen

A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

Four Columns Inn

Newfane

10/10 Excellent

Nettie

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

Sleep Woodstock Motel

Woodstock

10/10 Excellent

We were extremely impressed with the Sleep Woodstock Motel! If you get the chance- you need to book this place! Rooms were spacious and super clean, and the bed was extremely comfortable. Room had a fully stocked coffee bar; bathroom had plenty of towels, shampoo, conditioner, and lotion. Each room also has a retro mini fridge with a freezer, microwave, and coffeemaker. There is also a small eating area inside the room, and a table and chairs to sit outside your room on the patio. The room...

John

A large stone building with a steep roof, surrounded by dense forest and hills.

Castle Hill Resort And Spa

Cavendish

10/10 Excellent

STAFF I want to start by pointing out that the staff at the hotel were above and beyond PHENOMENAL, and I mean ALL THE STAFF. I spent the weekend up there and got stuck with some car problems in a blizzard and dealt with everybody on the staff there. They were some of the nicest people I have ever dealt with in the hospitality industry. When I say all the staff, I mean all the staff! DAY 1. The plow guy helped me get my car out of a spot when my snow chain broke and I couldn’t move. DAY 2...

Steven

A stone-clad building entrance with a covered patio and benches.

Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

Newbury

10/10 Excellent

Heidi

A multi-story hotel with a covered entrance, columns, and a well-lit facade.

Holiday Inn Express Hotel & Suites White River Junction by IHG

White River Junction

10/10 Excellent

Kristina

Find out more about Springfield

Search for holiday rentals in Springfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Springfield using one of the methods below:

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Look no further and take a look at our great range of rental properties in Springfield!

Frequently Asked Questions

Are there vacation rentals in Springfield?

Yes, we offer vacation rentals near top points of interest in Springfield, or you can go with a more secluded option if you want a relaxing place to stay. The ski slopes and restaurants are several reasons why visitors like Springfield. Make sure you have time to check out the local tours and festivals during your trip.

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

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This vacation home rental near Springfield is located on a lake and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Springfield?

With 10 Expedia vacation rentals, you're sure to find just the right place for your Springfield stay.

What can I see and do in Springfield?

Connecticut River and Skitchewaug State Wildlife Management Area are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Wilgus State Park and Muckross State Park.

What are vacation rentals like in Springfield?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Springfield. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for families.

Springfield Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Springfield vacation rentals

1. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

2. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

3. Explore the upper valley from this spacious Claremont Home

4. Charming Chester Farmhouse near Near VT Slopes

5. Renovated Vermont Retreat with mountain views near Okemo & Killington for 6

6. Fat Sheep Farm & Cabins

7. Cozy Resort Cabin! Hot-Tub Sauna Fire Pit Trails

8. Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

9. Game Room, Fire Pit & Views! Spacious Ludlow Home

10. Cozy Village Condo-Okemo Shuttle

11. 3 BR Luxury Condo at Castle Hill - 5 mi to Okemo

12. Lakefront Family Fun Retreat

13. Cozy Vermont Cabin at Trail End Ranch! The Best of VT is all around you!

14. Village Fireplace Shuttle Boot Warmers

15. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

16. Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

17. 3BR/2BA Near Okemo | Vermont Mountain Getaway

18. First-floor downtown studio near dining and gear shops, under a mile to Okemo

19. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

20. First-floor downtown condo, less than a mile from Okemo Mountain

Find vacation rentals that suit your style

Top Springfield Hotel Reviews

Best Western Springfield Hotel

10/10 Excellent

Find out more about Springfield

Frequently Asked Questions

Are there vacation rentals in Springfield?

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

How many vacation rentals are there in Springfield?

What can I see and do in Springfield?

What are vacation rentals like in Springfield?