Chesterfield holiday rentals

From simple studios to luxe lofts, find holiday rentals that are right for you on Airbnb.

Holiday rentals in Chesterfield

$334 NZD The Glow Room at Indian Hollow
26 reviews

The Glow Room at Indian Hollow is a history-rich 1850 post & beam barn, renovated in a light-filled, post modern style. Imagine getting out of your car, opening the screen do... read more
$209 NZD Serene Lakeside Cottage
20 reviews

Watch the stars come out over the lake at night and get away from it all in this renovated cabin that offers guests peace and quiet, open, modern floor plan with cathedral ceili... read more
$63 NZD Historical farm house
5 reviews

The 1780 Farm is adjacent to Pisgah Park, hiking, swimming, snow shoeing, cross country skiing and snow mobiling. We are 10 minutes from Bohemian downtown Brattleboro Vermont o... read more
$63 NZD The 1780 Farm
5 reviews

15 minutes to eclectic Brattleboro Vermont and Rockwellian New Hampshire. Adjacent to New Hampshires largest and smallest State Park. 35 acres to or relax. Our p... read more
$223 NZD Main House
3 reviews

A beautiful recently remodeled 3 bedroom 2.5 bath house with a full living room including a beautiful, pellet stove in the living room and adjoining covered deck with a stunnin... read more
$586 NZD Tyler House, steps to Lake Spofford
2 reviews

Tranquil, Relaxing, fun, magnificent sunrises and sunsets, premier NH lake, clean, great fishing, close to Brattleboro, VT and Keene, NH. Open house layout on ground floor, full... read more

Favourite Chesterfield holiday rentals

$63 NZD The 1780Farm
2 reviews

This is the Captains Berth The Farm is close to 15 minutes away from eclectic downtown Brattleboro Vermont or Rockwellian New Hampshire. Adjacent to New hampshires largest and... read more
$242 NZD #1 Rated B&B in New Hampshire
1 review

Romantic B&B on the border of New Hampshire & VT. Set in the Connecticut River Valley, guests enjoy beautiful views, 15 unique rooms or cottages & a delicious breakfast every mo... read more
$298 NZD Lake house with dock in quiet area
1 review

This lake is like Golden Pond, quiet, no motor boats allowed. House has picture windows overlooking lake. The dock is a perfect place to sip on coffee, throw out a fishing line... read more
$90 NZD Charming studio in renovated 19th century church
40 reviews

This spacious studio apartment is located in the former Swedish Congregational Church in historic Swedeville, a secluded hilly neighborhood built by Swedish immigrants in the 18... read more
$174 NZD Honeycrisp Cottage - A Tiny Timber Frame
19 reviews

Honeycrisp Cottage a Tiny Timberframe is a bright, energy efficient dwelling nestled on 9 acres overlooking a beautiful forested mountain & trails to explore along a brook. A pe... read more
$104 NZD Comfy Renovated School Bus
68 reviews

Full size school bus, nestled in the rolling hills of Vermont, within our farmstead filled with gardens, fields and forest. The Bus has a full size bed, gravity feed running wat... read more

More holiday rentals in Chesterfield

$67 NZD Downtown Hillside View
26 reviews

Downtown Hillside View offers a quick walk to downtown and some of the finest hiking trails in the area. Walk to Grafton Cheese House, Brattleboro Museum, Train Station, Library... read more
$174 NZD Meadowbrook Haven
34 reviews

Spacious one bedroom family friendly apartment with a cozy loft nestled on 140 + acres. A quiet get away in Brattleboro 2 miles from I-91 and minutes from dining, country advent... read more
$167 NZD Cozy cottage loft
52 reviews

Relax and recharge in our recently renovated Vermont cottage. Enjoy hardwood floors, wifi, a fully equipped kitchen, gorgeous natural light, views of surrounding hills and pond... read more
$313 NZD Lovely Brick Schoolhouse
44 reviews

This newly restored 1860's brick one-room school house with bedroom addition is situated 2 miles from the center of Putney, Vermont. Sleeps 4 in bedroom and living room pullout... read more
$61 NZD Maple St Guest Room, Brattleboro VT
87 reviews

Cozy and cheerful bedroom with two twin beds, shared bathrooms and access to kitchen. We are an active family of mom and teen who enjoy hosting and meeting travelers. Pets (gen... read more
$97 NZD Quiet St in Town, gardens, terrace
35 reviews

Private entry, up wide covered stairs to open and enclosed porches, into spacious eat-in kitchen which separates the BR with Queen bed, walk-in closet and sitting area, from the... read more

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