Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Cabin in Chesterfield

4.91 out of 5 average rating, 104 reviews

The Glow Room at Indian Hollow

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 door to a big porch that overlooks a leaping mountain brook, deep enough to dunk in. Then pass through the strap-hinged front door and into a glowing pine-panelled great room with giant windows, a big wood stove, 3 Chesterfield couches, dining area and kitchen. You see the forest all around you, but you're inside, ready to unwind. Upstairs, the loft features the master bedroom (sleeps 2, queen) and a reading/games room (can sleep 2, futon). Walking into the ell, you pass the bathroom, the 'room with no purpose,' and the guest bedroom (sleeps 2, futon) which opens onto the back deck, where the barbecue is, and the sound of the leaping waters. In summer the lawn is thick and lush, and you are surrounded with pines, birches, maples and mountains. Chauncey Brook forms the east border & offers a serene and ferny welcome; overlooking it, there's a beautiful firepit surrounded by log benches. The southern border is the Dead Branch Brook with its refreshing plunge pools. About a 1/4 mile downstream it joins the East Branch of the Westfield River, a federally-designated 'Wild and Scenic River.' We will provide you with maps and information about the area, which contains extraordinary opportunities for picnicking, fishing, hiking, biking, swimming, x-country skiing, snow-shoeing, photography and painting. And being alone, with someone you want to be alone with. This property is designed to inspire the maximum enjoyment of the 15+ square miles of open space that begins at its doorstep. The Glow Room is a launching pad. To amplify the quiet and help you unplug, there is no internet service (bring DVDs for your laptop). New cell phones work, but will drop out.

Nov 27 – Dec 4

R5,425 ZAR per night
Guest favorite

Guesthouse in Northampton

5.0 out of 5 average rating, 271 reviews

Mill River Cottage (pet friendly!)

Welcome to our peaceful and unique urban farm cottage. We are located in historic Florence, Massachusetts (a part of Northampton). While our place is no longer a working farm, the cottage was created many years ago to support the main dwelling. It has been modernized to offer every comfort while maintaining its cozy aesthetic. Free parking & lighted access to the cottage. The cottage is a private space where you can come and go as you please. Relax and unwind or head out to explore the area!

Dec 5 – 12

R2,288 ZAR per night
Guest favorite

Apartment in Greenfield

4.96 out of 5 average rating, 257 reviews

Mohawk Trail View/ private apt. no cleaning Fee

Apartment: Entrance, bathroom & driveway are all private. Backyard with gas bbq. Kitchenette has microwave, toaster oven, Keurig coffee maker & sink. 2 TV’s one in living room & bedroom. Netflix, Amazon Prime , HBO & Local programs. High speed internet. Bedroom has Queen bed & desk. Apt. Is 2 min's to Rt. 2 Mohawk Trail, Rt. 91, Supermarket, Restaurants & GCC. Less than 5 min's to Greenfield Center. <10 minutes to Deerfield Academy, Bement, Stonleigh. Berkshire East Resort Ski Area 24 minutes.

Jul 23 – 30

R1,985 ZAR per night

Popular amenities for Chesterfield vacation rentals

Other great vacation rentals in Chesterfield

Guest favorite

Guesthouse in Becket

4.93 out of 5 average rating, 257 reviews

Country Cabin

May 5 – 12

R2,305 ZAR per night
Guest favorite

Guest suite in Northampton

4.86 out of 5 average rating, 347 reviews

Cheery artist's studio in Florence

Aug 15 – 22

R1,844 ZAR per night
Guest favorite

Guesthouse in Amherst

4.95 out of 5 average rating, 473 reviews

Cozy get-away!

Oct 2 – 9

R1,941 ZAR per night
Guest favorite

Guest suite in Sunderland

4.96 out of 5 average rating, 170 reviews

Carib Home

Apr 27 – May 4

R1,970 ZAR per night
Guest favorite

Guest suite in Northampton

4.86 out of 5 average rating, 441 reviews

Separate apt, 1 mile from downtown, 1 guest only

Dec 21 – 28

R1,933 ZAR per night
Guest favorite

Guest suite in Easthampton

4.96 out of 5 average rating, 399 reviews

Goreytastic Private ApARTment @ the EMC

Aug 15 – 22

R1,783 ZAR per night
Guest favorite

Apartment in Goshen

4.94 out of 5 average rating, 360 reviews

Experience Three Sisters Sanctuary

Sep 30 – Oct 7

R4,053 ZAR per night
Guest favorite

Apartment in Amherst

4.98 out of 5 average rating, 255 reviews

The Bailey's Apartment

Oct 9 – 16

R1,934 ZAR per night
Guest favorite

Guest suite in Amherst

4.95 out of 5 average rating, 109 reviews

Bright, peaceful suite in great location!

Apr 30 – May 7

R1,685 ZAR per night
Guest favorite

Guest suite in Greenfield

4.94 out of 5 average rating, 143 reviews

Pristine Oasis with Private Bath

Nov 10 – 17

R1,337 ZAR per night
Guest favorite

Apartment in Shelburne Falls

4.96 out of 5 average rating, 286 reviews

Annies’ Place by The Bridge of Flowers ~

Jan 4 – 11

R1,942 ZAR per night
Guest favorite

Apartment in Pelham

4.99 out of 5 average rating, 125 reviews

Pelham 2nd floor Apartment

Apr 3 – 10

R1,756 ZAR per night

Destinations to explore