Vacation rentals in Town of Rockingham

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Top-rated vacation rentals in Town of Rockingham

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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 $.

May 6 – 13

G$20,929 GYD per night

Guest favorite

Cabin in Londonderry

4.93 out of 5 average rating, 308 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond in S Londonderry, VT. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery and hiking right outside your front door. The Cabin has an open floor plan with a galley kitchen, dining/living area with pullout futon couch & 1 full bathroom. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Nov 5 – 12

G$21,361 GYD per night

Guest favorite

Home in Putney

4.94 out of 5 average rating, 337 reviews

Vermont Botanical Studio Apartment

This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.

Mar 5 – 12

G$23,065 GYD per night

Guest favorite

Cabin in Marlow

4.97 out of 5 average rating, 109 reviews

The Birches Cabin, at home in the woods!

The Birches is situated on 10 secluded acres, where guests will enjoy the privacy and scenery the cabin offers. Built in 2020 and designed to accommodate guests. During your stay take a walk on the property, read a book, enjoy a glass a wine, cook a fine meal, and stare at the stars. Centrally between Keene and the Sunapee region, guests have many options on how to enjoy their days such as Skiing, Hiking, Paddling, and Snow tubing. This is a vacation spot, that can be enjoyed all year.

Sep 20 – 27

G$24,824 GYD 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.

Apr 15 – 22

G$19,030 GYD 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.

Mar 10 – 17

G$32,321 GYD per night

Superhost

Home in Town of Rockingham

4.89 out of 5 average rating, 113 reviews

Beautiful Home in the Mountains - The Fox & Owl

When you walk into the Fox and Owl, your stress and anxiety get left outside! The Fox and Owl is perfect for couples and solo adventurers alike - anyone who wants a cozy house in a perfect location for exploring everything southern Vermont has to offer: Hiking, kayaking, skiing, snow-shoeing, bicycling (road, mountain, fat tire), bird and foliage watching, antique and craft shopping, farmers markets and breweries, great local food and great local fishing are all within just a few miles!

Jul 7 – 14

G$41,862 GYD per night

Guest favorite

Barn in Chester

4.99 out of 5 average rating, 493 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.

Oct 1 – 8

G$21,528 GYD 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!

Jul 2 – 9

G$33,584 GYD per night

Guest favorite

Apartment in Townshend

4.94 out of 5 average rating, 203 reviews

Private Apt. on Farm, great views and Hot tub,

Self-contained apt with fantastic views, outside deck & private entrance with keypad lock. Two queen bedrooms and queen sleeping loft, kitchen and open plan living room. Located on a historic 38-acre working farm. If you need more space we have an adjoining apartment that sleeps 5. Apartment is above garage and attached to the main farmhouse. Pls note pricing is based on up to four guests; add'l $25/person/night up to max 6 guests added automatically.

Dec 9 – 16

G$32,353 GYD per night

Guest favorite

Cottage in Windsor

4.97 out of 5 average rating, 317 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.

Dec 17 – 24

G$28,979 GYD per night

Guest favorite

Apartment in Andover

4.98 out of 5 average rating, 386 reviews

Private Hilltop farm apartment

Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!

Sep 15 – 22

G$23,377 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Town of Rockingham vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Town of Rockingham's top sights

The Vermont Country Store Rockingham55 locals recommend

Dari Joy6 locals recommend

Athens Pizza House Inc6 locals recommend

Lola's Pizzeria3 locals recommend

Bellows Falls Opera House17 locals recommend

Joy Wah Restaurant6 locals recommend

Other great vacation rentals in Town of Rockingham

Guest favorite

Guesthouse in Putney

4.95 out of 5 average rating, 322 reviews

A Vermont Carriage House

Apr 12 – 19

G$34,557 GYD per night

Guest favorite

Guest suite in Brattleboro

4.94 out of 5 average rating, 518 reviews

Charming studio in renovated 19th century church.

Nov 29 – Dec 6

G$19,434 GYD per night

Guest favorite

Apartment in Brattleboro

4.95 out of 5 average rating, 150 reviews

Contemporary forest eco-retreat, mountain views

May 21 – 28

G$24,697 GYD per night

Guest favorite

Apartment in Londonderry

4.94 out of 5 average rating, 333 reviews

Cozy Suite in a Historic Building Near Ski Resorts

May 29 – Jun 5

G$25,296 GYD per night

Guest favorite

Apartment in Dublin

4.96 out of 5 average rating, 182 reviews

Private Dublin apartment nestled in the woods

Sep 24 – Oct 1

G$22,725 GYD per night

Guest favorite

Loft in Town of Rockingham

5.0 out of 5 average rating, 32 reviews

Saxtons River Studio apartment

Feb 14 – 21

G$23,890 GYD per night

Guest favorite

Vacation home in Town of Rockingham

4.96 out of 5 average rating, 53 reviews

Cozy studio at Leslie's Tavern in Rockingham

Sep 4 – 11

G$31,719 GYD per night

Guest favorite

Apartment in Town of Rockingham

4.89 out of 5 average rating, 65 reviews

Lovely light-filled 2 bedroom flat

May 16 – 23

G$24,824 GYD per night

Show all

Quick stats about vacation rentals in Town of Rockingham

Total rentals
50 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
3.6K reviews
Nightly prices starting at
G$12,506 GYD before taxes and fees

Frequently Asked Questions

Are there pet-friendly vacation rentals in Town of Rockingham?
Four-legged friends are welcome in Town of Rockingham. Choose from more than 20 vacation rentals for guests traveling with pets.
Do house rentals in Town of Rockingham have wifi?
Absolutely! We offer over 10 house rentals with wifi in Town of Rockingham. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Town of Rockingham?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with a kitchen, 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 Town of Rockingham have free parking?
Absolutely! We offer over 10 house rentals with free parking in Town of Rockingham. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Town of Rockingham?
Yes! Work meets play with ease at over 30 vacation rentals in Town of Rockingham featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Town of Rockingham?
Experience the best of Town of Rockingham with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Town of Rockingham have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Town of Rockingham. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Town of Rockingham have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Town of Rockingham. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Town of Rockingham

Top-rated vacation rentals in Town of Rockingham

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Town of Rockingham vacation rentals

Stay near Town of Rockingham's top sights

Other great vacation rentals in Town of Rockingham

Guesthouse in Putney

Guest suite in Brattleboro

Apartment in Brattleboro

Apartment in Londonderry

Apartment in Dublin

Loft in Town of Rockingham

Vacation home in Town of Rockingham

Apartment in Town of Rockingham

Quick stats about vacation rentals in Town of Rockingham

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 pet-friendly vacation rentals in Town of Rockingham?

Do house rentals in Town of Rockingham have wifi?

What are the most popular amenities for Apartment Rentals in Town of Rockingham?

Do house rentals in Town of Rockingham have free parking?

Are there vacation rentals with a dedicated workspace in Town of Rockingham?

How much does it cost to stay in house rentals in Town of Rockingham?

Do apartment rentals in Town of Rockingham have a kitchen?

Do house rentals in Town of Rockingham have air conditioning?

Destinations to explore