Holiday rentals in Springfield

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Top-rated holiday rentals in Springfield

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Guest favourite

Flat 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 $.

30 Apr – 7 May

$137 SGD per night

Guest favourite

Guest house 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.

14–21 Mar

$124 SGD per night

Guest favourite

Flat 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.

8–15 Sep

$211 SGD per night

Superhost

Apartment 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.

19–26 May

$150 SGD per night

Guest favourite

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.

31 May – 7 Jun

$135 SGD per night

Guest favourite

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.

4–11 Nov

$135 SGD per night

Guest favourite

Guest suite in Chester

4.92 out of 5 average rating, 154 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!

21–28 Jul

$198 SGD per night

Guest favourite

Flat 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.

4–11 Sep

$167 SGD per night

Guest favourite

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.

13–20 Nov

$185 SGD per night

Guest favourite

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.

29 Sep – 6 Oct

$149 SGD per night

Guest favourite

Flat in Weathersfield

4.97 out of 5 average rating, 109 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.

22–29 Apr

$213 SGD per night

Guest favourite

Flat in Claremont

4.88 out of 5 average rating, 110 reviews

Beautiful 1 bedroom apartment with balcony

Bienvenue chez nous! Experience comfort and modern beauty in this completely renovated apartment attached to a historic Victorian home. The one bedroom apartment has a private bathroom and your own balcony to enjoy. Close to popular skiing areas of Mt Sunapee (20 minutes) and Okemo (35 minutes), in addition to enjoying local hiking and cycling at Mt Ascutney, Moody Park, and Arrowhead.

15–22 Jul

$119 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Springfield holiday 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 holiday rentals in Springfield

Guest favourite

Place to stay in Town of Rockingham

4.92 out of 5 average rating, 61 reviews

Romantically cheerful one-bedroom suite

27 Jun – 4 Jul

$121 SGD per night

Guest favourite

Farm stay in Chester

4.98 out of 5 average rating, 40 reviews

Rivers Edge Farm’s Cozy Cabin

10–15 Aug

$130 SGD per night

Guest favourite

Home in Chester

5.0 out of 5 average rating, 16 reviews

Cozy 1850 farmhouse in Stone Village of Chester

24–31 Jan

$173 SGD per night

Guest favourite

Home in Springfield

4.98 out of 5 average rating, 60 reviews

Luxury Mid-Century Modern Vermont Home, Okemo View

3–10 May

$619 SGD per night

Superhost

Holiday home in Cavendish

4.84 out of 5 average rating, 32 reviews

Cozy 1 bd Apt Minutes to Okemo & Pet Friendly

29 May – 5 Jun

$130 SGD per night

Guest favourite

Home in Springfield

5.0 out of 5 average rating, 45 reviews

1794 Pioneer House - Renovated, No Cleaning Fee!

8–15 Sep

$379 SGD per night

Guest favourite

Farm stay in Baltimore

4.92 out of 5 average rating, 96 reviews

Hawk Mtn Farm's lovely one bedroom apartment!

22–29 Jun

$155 SGD per night

Guest favourite

Apartment in Ludlow

4.93 out of 5 average rating, 54 reviews

Ground Floor, Okemo True Ski-in/Ski-Out

26 Aug – 2 Sep

$145 SGD per night

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Quick stats about holiday 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	$55 SGD before taxes and fees

Holiday rentals in Springfield

Top-rated holiday rentals in Springfield

Flat in Springfield

Guest house in Springfield

Flat in Bellows Falls

Apartment in Ludlow

Barn in Chester

Home in Ludlow

Guest suite in Chester

Flat in Weathersfield

Cottage in Windsor

Guest suite in West Windsor

Flat in Weathersfield

Flat in Claremont

Holiday rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Springfield holiday rentals

Stay near Springfield's top sights

Other great holiday rentals in Springfield

Place to stay in Town of Rockingham

Farm stay in Chester

Home in Chester

Home in Springfield

Holiday home in Cavendish

Home in Springfield

Farm stay in Baltimore

Apartment in Ludlow

Quick stats about holiday rentals in Springfield

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

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