Vacation rentals in Springfield

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Top-rated vacation rentals in Springfield

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Guest favorite

Apartment in Springfield

4.91 out of 5 average rating, 222 reviews

Farm Barn apt. 3 bedr, 2 bath, fiberoptic internet

Getaway for families, couples or groups. Apt. in our Barn. High speed internet, so ideal for "work from home". Full kitchen with oven, microwave, dishwasher, big fridge , 3 bedrooms, 2 baths, Dining/Living room with TV ( Antenna, no cable, Roku: bring your passwords for Netflix..) Fields, forest, hill and river on our property. We allow one friendly dog at a time but it is not allowed to stay in the apt. by itself (daycare in Spgf avbl). Please add the dog to your booking for the one time 35 $.

Apr 28 – May 5

ﺩ.ﺇ369 per night

Guest favorite

Guesthouse in Springfield

4.86 out of 5 average rating, 321 reviews

Connecticut River-Cozy Cottage

This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.

Mar 6 – 13

ﺩ.ﺇ335 per night

Guest favorite

Apartment in Bellows Falls

4.95 out of 5 average rating, 182 reviews

Village Flat with Antique Billiards

Charming and spacious first floor, 3 Bedroom, 1 Full Bath apartment. Sleeps 5 (1 King, 1 Queen and 1 twin). It is nestled in the center of the Bellows Falls village, a short 5-minute walk to downtown, where you will find great little shops and eateries. We are centrally located in Southern Vermont ~ 40 min from several ski areas (Okemo, Magic, Bromley, Stratton, etc.) about one hour from Killington Resort, Mount Snow, and Mount Sunapee (NH), and ~ 20 mins from Brattleboro, VT, or Keene, NH.

Nov 5 – 12

ﺩ.ﺇ570 per night

Superhost

Condo in Ludlow

4.92 out of 5 average rating, 121 reviews

All Season Lovely and Zen Okemo Mt Lodge Condo

Tired of city life and want a fresh breath? Feel the call from nature while also desiring some sporty fun? Come enjoy our lovely and Zen Condo right at the foot of beautiful Okemo! True ski-in/ski-out in the winter. Enjoy your warm ski day lunch by sitting next to the wood-burning fireplace*, while watching all the activities on the slope. In the warm weather, enjoy the beautiful hiking trails and golf course that Okemo offers, as well as water activities at the nearby lakes and rivers.

May 19 – 26

ﺩ.ﺇ383 per night

Guest favorite

Barn in Chester

4.99 out of 5 average rating, 492 reviews

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

Sep 22 – 29

ﺩ.ﺇ374 per night

Guest favorite

Home in Ludlow

4.92 out of 5 average rating, 139 reviews

149 Upper Crossroad Unit A

Renovated in the Summer of 2018, the Townhomes at Clock Tower are a beautiful, spacious year-mountain retreat. It sleeps 8 and has been beautifully appointed, with 2 Family rooms, 3 bedrooms, 2 bathrooms, a large open concept Kitchen, and Dining room with Gas Stove. The kitchen boasts granite countertops, dishwasher, with essentials. A short 5-minute walk to the Okemo Clock Tower Base Lodge, or a weekend/holiday shuttle that stops at the home for those who prefer not to walk it.

Jun 17 – 24

ﺩ.ﺇ365 per night

Guest favorite

Guest suite in Chester

4.91 out of 5 average rating, 155 reviews

Chester Carriage House-Cozy-Quintessential Vermont

Our Carriage House is less than a mile to charming Chester Village-enjoy quaint restaurants and pubs, antique shops, art galleries, yoga studio and a country market. Explore southern Vermont’s famous hiking trails, world class skiing, farms, winding rivers + breweries. Close proximity to the best of Vermont's ski resorts! (Magic Mountain, Bromley, Stratton, Okemo and Killington) Come experience why Chester has been voted one of the top 10 most beautiful towns in Vermont!

Jun 2 – 9

ﺩ.ﺇ556 per night

Guest favorite

Apartment in Weathersfield

4.99 out of 5 average rating, 157 reviews

The Loft at Weathersfield

Close to Okemo, The Loft at Weathersfield, is just 1/2 hour south of Woodstock / Hanover area and 22 minutes from Okemo Mountain. The Loft, is located in a private agricultural setting with easy access to Vermont's best biking, hiking, fly fishing, skiing, and many equine trails. The loft is 900 square feet with a kitchen/dining room, living room, full bath, one bedroom with a queen bed and one twin bed. There is a spacious deck off the kitchen and a car port underneath.

Nov 26 – Dec 3

ﺩ.ﺇ450 per night

Guest favorite

Cottage in Windsor

4.97 out of 5 average rating, 316 reviews

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins.

Nov 26 – Dec 3

ﺩ.ﺇ508 per night

Guest favorite

Condo in Ludlow

4.92 out of 5 average rating, 122 reviews

Okemo Ski-in/Ski-out, Steps to lift Condo

Just steps of walk to the amazing Okemo slopes, C Building is the closest property to the A-Quad/B-Quad lift and this building offers convenient parking right downstairs and free wi-fi (dedicated Xfinity modem, no issue video conference). You’ll love this cozy place with hardwood floor and private balcony and sunshine after skiing. Great sun exposure. Fireplace has been updated to electric fireplace starting from 2023-2024 season.

Jul 27 – Aug 3

ﺩ.ﺇ370 per night

Guest favorite

Guest suite in West Windsor

4.9 out of 5 average rating, 102 reviews

Newly renovated private space on Ascutney Trails

Newly renovated space on Ascutney trails--walking distance Ascutney Outdoors Center, hotel, restaurant, skiing, and Brownsville Butcher & Pantry. Trail access in back yard with miles of hiking, mountain biking, running and skiing. Parking for 2 cars. Close to Woodstock shops and Okemo adventure center. Private keycode entrance with self-check in. Microwave, refrigerator, Keurig, coffee and tea provided. Fast wifi.

Dec 8 – 15

ﺩ.ﺇ362 per night

Guest favorite

Apartment in Weathersfield

4.97 out of 5 average rating, 110 reviews

Cute VT Bungalow With 180 Degree View of NH

Located on a quiet country dirt road you will find this cozy apartment perfect for a weekend getaway. A short walk and you will be amazed at the 360 degree views of Vermont and New Hampshire. Centrally located near Okemo, Sunapee and Killington mountains, ski all 3 mountains in a weekend. Explore covered bridges, walking trails, scenic bike rides, or tubing on the Connecticut River.

Apr 24 – May 1

ﺩ.ﺇ573 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Springfield vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Springfield's top sights

Black Rock Steakhouse24 locals recommend

Springfield Cinemas 39 locals recommend

Springfield Royal Diner6 locals recommend

Shaw's8 locals recommend

Riverside Restaurant3 locals recommend

The Sumner House3 locals recommend

Other great vacation rentals in Springfield

Guest favorite

Cabin in West Windsor

4.98 out of 5 average rating, 205 reviews

Sunset Cabin - your private romantic hideaway

Jul 2 – 9

ﺩ.ﺇ570 per night

Guest favorite

Farm stay in Chester

4.98 out of 5 average rating, 40 reviews

Rivers Edge Farm’s Cozy Cabin

Apr 30 – May 5

ﺩ.ﺇ317 per night

Guest favorite

Home in Chester

5.0 out of 5 average rating, 16 reviews

Cozy 1850 farmhouse in Stone Village of Chester

Jan 26 – Feb 2

ﺩ.ﺇ466 per night

Guest favorite

Place to stay in Town of Rockingham

4.92 out of 5 average rating, 61 reviews

Romantically cheerful one-bedroom suite

Aug 15 – 22

ﺩ.ﺇ366 per night

Superhost

Vacation home in Cavendish

4.84 out of 5 average rating, 32 reviews

Cozy 1 bd Apt Minutes to Okemo & Pet Friendly

May 31 – Jun 7

ﺩ.ﺇ308 per night

Guest favorite

Home in Springfield

4.98 out of 5 average rating, 60 reviews

Luxury Mid-Century Modern Vermont Home, Okemo View

May 3 – 10

ﺩ.ﺇ1,668 per night

Guest favorite

Farm stay in Baltimore

4.92 out of 5 average rating, 96 reviews

Hawk Mtn Farm's lovely one bedroom apartment!

Jun 24 – Jul 1

ﺩ.ﺇ419 per night

Superhost

Guest suite in Chester

4.84 out of 5 average rating, 44 reviews

Adorable, Cozy 2 bedroom apartment walk to village

Nov 5 – 12

ﺩ.ﺇ518 per night

Show all

Quick stats about vacation rentals in Springfield

Total rentals
40 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.2K reviews
Nightly prices starting at
ﺩ.ﺇ147 before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Springfield?
Yes! Work meets play with ease at over 20 vacation rentals in Springfield featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Springfield?
Four-legged friends are welcome in Springfield. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Springfield have wifi?
Absolutely! We offer over 10 house rentals with wifi in Springfield. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Springfield have free parking?
Absolutely! We offer over 10 house rentals with free parking in Springfield. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Springfield?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with air conditioning, over 10 homes with free parking, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Springfield have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Springfield. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in hotel rentals in Springfield?
Experience the best of Springfield with our hotel rentals, starting at about $180 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Springfield have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Springfield. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Springfield

Top-rated vacation rentals in Springfield

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Springfield vacation rentals

Stay near Springfield's top sights

Other great vacation rentals in Springfield

Cabin in West Windsor

Farm stay in Chester

Home in Chester

Place to stay in Town of Rockingham

Vacation home in Cavendish

Home in Springfield

Farm stay in Baltimore

Guest suite in Chester

Quick stats about vacation rentals in Springfield

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Springfield?

Are there pet-friendly vacation rentals in Springfield?

Do house rentals in Springfield have wifi?

Do house rentals in Springfield have free parking?

What are the most popular amenities for House Rentals in Springfield?

Do house rentals in Springfield have a kitchen?

How much does it cost to stay in hotel rentals in Springfield?

Do house rentals in Springfield have air conditioning?

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