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32 Houses

(1) Excellent 

12

Classic New England Farm House

New Hampshire / Chesterfield

Chesterfield b and b

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child Friendly

Price per night from

$52

Price per night from

$52

12

Historical Farm House

New Hampshire / Chesterfield

Chesterfield b and b

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$52

Responds fast!
avg. 3 hours 53 minutes

Price per night from

$52

(4) Excellent 

40

Affordable Spacious Vacation Home on Lake Spofford

New Hampshire / Chesterfield

Chesterfield house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Beach / lakeside relaxation
  • Ask about children
  • Air conditioning

Price per night from

$120

Price per night from

$120

Great rentals within 20 miles that match your search

Distance approx 19.33 km from Chesterfield

31

Classic, dog-friendly cabin in the woods w/ private deck

Vermont / Dover

Dover house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Pet Friendly

Price per night from

$123

Price per night from

$123

Distance approx 19.78 km from Chesterfield

38

'John's Farmhouse in Mount Snow' on 120 Acres!

Vermont / Whitingham

Whitingham house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Ski
  • Child Friendly
  • Pet Friendly

Price per night from

$344

Responds fast!
avg. 11 minutes

Price per night from

$344

Distance approx 7.76 km from Chesterfield

30

Colonial Keene House on 7 Acres w/ Pool!

New Hampshire / Keene

Keene house

9 18 min stay varies

  • 9 bedrooms
  • sleeps 18
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$604

Responds fast!
avg. 11 minutes

Price per night from

$604

Distance approx 17.87 km from Chesterfield

23

Lakeside Year Round Totally Renovated Home

Vermont / Wilmington

Wilmington house

5 10 2 nights min

  • 5 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly

Price per night from

$690

Price per night from

$690

Distance approx 4.25 km from Chesterfield

28

NEW! Beautiful Log House 3.5 Mi. to Spofford Lake!

New Hampshire / Westmoreland

Westmoreland house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$161

Responds fast!
avg. 10 minutes

Price per night from

$161

Distance approx 16.07 km from Chesterfield

(1) Excellent 

7

PARADISE on EARTH! - Historic 4BR Farmhouse

Vermont / West Halifax

West Halifax house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly
  • Ask about pets
  • Private garden

Price per night from

$328

Price per night from

$328

Distance approx 17.93 km from Chesterfield

9

Private Mountain Getaway

Vermont / Dover

Dover house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$138

Responds fast!
avg. 3 hours 47 minutes

Price per night from

$138

Distance approx 6.63 km from Chesterfield

(2) Average 

5

Adorable Studio apartment in Brattleboro

Vermont / Brattleboro

Brattleboro apartment

2 1 night min

  • sleeps 2
  • 1 night min
  • Ask about children
  • Pet Friendly

Price per night from

$155

Price per night from

$155

Distance approx 15.45 km from Chesterfield

20

Casual lux near Hermitage Club & Four Columns Inn

Vermont / South Newfane

South Newfane villa

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 10 mi
  • Ski
  • Ask about children

Price per night from

$1,723

Price per night from

$1,723

Distance approx 18.26 km from Chesterfield

24

Cabin w/Deck - Mins to Mt. Snow & Lake Raponda!

Vermont / Wilmington

Wilmington log cabin

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly

Price per night from

$155

Responds fast!
avg. 11 minutes

Price per night from

$155

Distance approx 7.78 km from Chesterfield

16

Church sanctuary

Vermont / West Dummerston

West Dummerston house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Ask about children

Price per night from

$298

Price per night from

$298

Distance approx 13.78 km from Chesterfield

(7) Excellent 

5

Vermont Log Cabin available for weekend and weekly

Vermont / Guilford

Guilford log cabin

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Pet Friendly
“Hidden Gem” My boyfriend and I had the pleasure of staying at this beautiful cabin a couple of weeks ago and honestly, I can't say enough good things about it! For starters, it is gorgeous both inside and out and much bigger than we had anticipated.
…see more

Price per night from

$126

Price per night from

$126

Distance approx 18.94 km from Chesterfield

21

New Lakefront Cedar Log Home

Vermont / Wilmington

Wilmington chalet

3 12 2 nights min

  • 3 bedrooms
  • sleeps 12
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary

Price per night from

$516

Responds fast!
avg. 1 hour 43 minutes

Price per night from

$516

Distance approx 10.91 km from Chesterfield

(4) Excellent 

24

Romantic Vermont Vacation Cabin with View

Vermont / Newfane

Newfane cottage

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 8 mi
  • Child Friendly
  • Private garden

Price per night from

$173

Responds fast!
avg. 2 hours 21 minutes

Price per night from

$173

Distance approx 18.17 km from Chesterfield

(12) Excellent 

20

Lake Warren-Alstead-Walpole-Keene- Spring Summer

New Hampshire / Alstead

Alstead cottage

4 5 3 nights min

  • 4 bedrooms
  • sleeps 5
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Child Friendly
“Unplug , unwind and relax” Cute , clean and refreshingly quiet. My wife and I thoroughly enjoyed our week on the lake (the dogs did as well). The nearby hiking, kayaking, and local produce were great! Thanks for the memories Lake Warren!!
…see more

Price per night from

$201

Price per night from

$201

Distance approx 19.5 km from Chesterfield

28

Renovated 1950's Farmhouse on 300 Acres in Grafton

Vermont / Grafton

Grafton house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$287

Responds fast!
avg. 51 minutes

Price per night from

$287

Distance approx 2.21 km from Chesterfield Show on Map

7

Historic Lakefront Spofford Cottage

New Hampshire / Spofford

Spofford house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Private garden

Price per night from

$458

Price per night from

$458

Distance approx 10.8 km from Chesterfield

(1) Excellent 

15

3 BDR Farmhouse on Tranquil 105 acre Organic Farm

New Hampshire / Walpole

Walpole house

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Nearest beach 8 mi
  • Child Friendly
  • Air conditioning

Price per night from

$304

Price per night from

$304

Distance approx 16.15 km from Chesterfield

(7) Excellent 

26

Log Cabin, 4 BR / 2 Bath Minutes to Mount Snow!

Vermont / Dover

Dover log cabin

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Private garden

Price per night from

$228

Responds fast!
avg. 3 hours 57 minutes

Price per night from

$228

Distance approx 17.76 km from Chesterfield

21

Mountain Side

Vermont / Dover

Dover house

3 12 2 nights min

  • 3 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$862

Responds fast!
avg. 1 hour 47 minutes

Price per night from

$862

Distance approx 8.63 km from Chesterfield

(4) Excellent 

21

Beautiful Lake Side Getaway, Quiet, and Peaceful

New Hampshire / Winchester

Winchester apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 160 mi
  • Ask about children
“Relaxing vacation” We vacationed here for the first two weeks of July. Bill and Sandy were fabulous hosts. They were attentive to our needs and generous with their time taking us out in their boat to view the fireworks. The space is decorated taste
…see more

Price per night from

$101

Price per night from

$101

Distance approx 17.65 km from Chesterfield

24

Rustic East Dover House w/ Pond Near Mount Snow!

Vermont / Dover

Dover house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Ski
  • Child Friendly
  • Pet Friendly

Price per night from

$247

Responds fast!
avg. 10 minutes

Price per night from

$247

Distance approx 11.23 km from Chesterfield

17

Stay at a Craft Brewery

New Hampshire / Winchester

Winchester apartment

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Pet Friendly

Price per night from

$115

Price per night from

$115

Distance approx 19.7 km from Chesterfield

24

Family Home w/Game Room & Sauna-Mins to Mt. Snow!

Vermont / Dover

Dover house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ski
  • Child Friendly

Price per night from

$373

Responds fast!
avg. 10 minutes

Price per night from

$373

Distance approx 18.63 km from Chesterfield

26

"Bunny Hill Chalet" Lodge Style Home Near Mt Snow

Vermont / Dover

Dover house

4 14 2 nights min

  • 4 bedrooms
  • sleeps 14
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$690

Price per night from

$690

Distance approx 8.39 km from Chesterfield

15

Stunning Forest Lake Home with Hot Tub open all Yr

New Hampshire / Winchester

Winchester house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$224

Responds fast!
avg. 2 hours 35 minutes

Price per night from

$224

Distance approx 1.68 km from Chesterfield Show on Map

(32) Very Good 

40

Beautiful House overlooking Spofford Lake

New Hampshire / Spofford

Spofford house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Ask about children
  • Air conditioning

Price per night from

$184

Price per night from

$184

Distance approx 16.07 km from Chesterfield

15

Enchanting Rockwood Pond Home with Hot Tub!

New Hampshire / Fitzwilliam

Fitzwilliam house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$224

Responds fast!
avg. 2 hours 35 minutes

Price per night from

$224

Distance approx 1.72 km from Chesterfield Show on Map

(1) Excellent 

26

Steps to the sandy beach

New Hampshire / Spofford

Spofford house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Ask about children
  • Air conditioning

Price per night from

$149

Price per night from

$149