A town square with historic buildings, a crosswalk, and a street lined with parked cars.

Springfield Vacation Rentals

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Our top choices for Springfield vacation rentals

1. Cozy Village Condo-Okemo Shuttle

Cozy Village Condo-Okemo Shuttle
Ludlow
9.8 out of 10, Exceptional, (89 reviews)
"Great place to stay, very easy to get to. A cozy and comfortable place, that is always clean. There are postings and labels throughout, which is very helpful. Hosts are great and make the experience very easy. Oh and the bed is amazing!!"
United States
Vanessa W.
The price is CA $119
CA $362 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Village Condo-Okemo Shuttle

2. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Chester
10.0 out of 10, Exceptional, (6 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is CA $762
CA $1,351 total
includes taxes & fees
Nov 9 - Nov 10
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

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

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (175 reviews)
"We had such a great time! Those is a well taken care of, clean, cozy property. We would absolutely visit again!!"
United States
Kathy H.
The price is CA $240
CA $517 total
includes taxes & fees
Nov 9 - Nov 10
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

4. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (15 reviews)
"This property was extremely beautiful and peaceful. Loved being able to walk around the farm and say hi to the animals. The views of the mountains from the cabin or gorgeous, we enjoyed having our coffee on the porch each morning. Having fresh eggs and scones in our cabin upon arrival was a very nice surprise. Will definitely be staying there again."
United States
Brenda
The price is CA $159
CA $250 total
includes taxes & fees
Nov 17 - Nov 18
Fat Sheep Farm & Cabins

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

Renovated Vermont Retreat with mountain views near Okemo & Killington for 6
Cavendish
10.0 out of 10, Exceptional, (3 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
The price is CA $229
CA $706 total
includes taxes & fees
Nov 9 - Nov 10
Renovated Vermont Retreat with mountain views near Okemo & Killington for 6

6. Peaceful Stay w/ Pond & Massage Chair | Near Okemo

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
The price is CA $168
CA $620 total
includes taxes & fees
Nov 9 - Nov 10
Peaceful Stay w/ Pond & Massage Chair | Near Okemo

7. Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.4 out of 10, Exceptional, (22 reviews)
"Beautiful classic farmhouse in lovely neighbourhood."
United States
Kimberly B.
The price is CA $266
CA $533 total
includes taxes & fees
Nov 9 - Nov 10
Charming Chester Farmhouse near Near VT Slopes

8. Condo a short walk to the Sachem trail with seasonal pool and tennis

Condo a short walk to the Sachem trail with seasonal pool and tennis
Ludlow
The price is CA $88
CA $405 total
includes taxes & fees
Nov 11 - Nov 12
Condo a short walk to the Sachem trail with seasonal pool and tennis

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

Cozy Resort Cabin! Hot-Tub Sauna Fire Pit Trails
Cavendish
10.0 out of 10, Exceptional, (58 reviews)
"The cabins are amazing, everything you need for a great weekend! I will be back for sure!"
United States
Joe C.
The price is CA $281
CA $559 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Resort Cabin! Hot-Tub Sauna Fire Pit Trails

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

Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
The price is CA $82
CA $317 total
includes taxes & fees
Nov 11 - Nov 12
Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

11. Explore the upper valley from this spacious Claremont Home

Explore the upper valley from this spacious Claremont Home
Claremont
10.0 out of 10, Exceptional, (1 review)
"Nice place."
United States
Michael R.
The price is CA $424
CA $500 total
includes taxes & fees
Nov 9 - Nov 10
Explore the upper valley from this spacious Claremont Home

12. Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
Newport
10.0 out of 10, Exceptional, (5 reviews)
"Had a lot here to use and The place was very cute. It’s good if you have small kids they have a lot for that sort of thing. Very clean as well"
United States
sean c.
The price is CA $183
CA $574 total
includes taxes & fees
Nov 10 - Nov 11
Lakefront Family Fun Retreat

13. Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts

Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts
Clock Tower Base Area
8.8 out of 10, Excellent, (81 reviews)
"It was a perfect location and had everything we needed for a great stay."
United States
Danna K.
The price is CA $118
CA $371 total
includes taxes & fees
Nov 11 - Nov 12
Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts

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

First-floor downtown studio near dining and gear shops, under a mile to Okemo
Ludlow
8.8 out of 10, Excellent, (14 reviews)
"This place was so close to Okemo, and walking distance to the local pub and restaurants."
United States
Brian
The price is CA $158
CA $433 total
includes taxes & fees
Nov 11 - Nov 12
First-floor downtown studio near dining and gear shops, under a mile to Okemo

15. Downtown Ludlow condo with electric fireplace, shuttle stop across the street

Downtown Ludlow condo with electric fireplace, shuttle stop across the street
Ludlow
8.8 out of 10, Excellent, (27 reviews)
"Easy stay. Great location."
United States
Zach S.
The price is CA $167
CA $385 total
includes taxes & fees
Nov 11 - Nov 12
Downtown Ludlow condo with electric fireplace, shuttle stop across the street

16. Compact downtown studio condo with kitchenette near the Okemo slopes

Compact downtown studio condo with kitchenette near the Okemo slopes
Ludlow
8.6 out of 10, Excellent, (34 reviews)
"the home was clean and very nice. "
United States
Frank R.
The price is CA $158
CA $329 total
includes taxes & fees
Nov 11 - Nov 12
Compact downtown studio condo with kitchenette near the Okemo slopes

17. 2BR Duplex Villa w/ Balcony | Game Room + Fire Pit

2BR Duplex Villa w/ Balcony | Game Room + Fire Pit
Brownsville
The price is CA $329
CA $389 total
includes taxes & fees
Nov 16 - Nov 17
2BR Duplex Villa w/ Balcony | Game Room + Fire Pit

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

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (26 reviews)
"Great location, and comfortable for the whole family. Everyone in the enjoyed the open living room and dining room, plus the privacy of their own bedroom space. "
United States
Ania H.
The price is CA $424
CA $728 total
includes taxes & fees
Nov 14 - Nov 15
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

19. Adventure Cabin Hot Tub Sauna Trails Game Area

Adventure Cabin Hot Tub Sauna Trails Game Area
Cavendish
10.0 out of 10, Exceptional, (29 reviews)
"A very clean and modern cabin. Loved the amenities like the paddle boards, kayaks and hot tub.!"
United States
Katherine B.
The price is CA $281
CA $559 total
includes taxes & fees
Nov 11 - Nov 12
Adventure Cabin Hot Tub Sauna Trails Game Area

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

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (114 reviews)
"Wendi was very responsive when I had questions. We enjoyed our weekend getaway. Great location we walked into town to the Farmers Market Sunday."
United States
Tina l.
The price is CA $297
CA $673 total
includes taxes & fees
Nov 18 - Nov 19
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
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 Springfield Hotel Reviews

Find out more about Springfield

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Springfield. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.