Holiday rentals in Pittsfield

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Top-rated holiday rentals in Pittsfield

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

Guest favourite

Guest suite in Strafford

4.87 out of 5 average rating, 259 reviews

The West Wing: A perfect romantic getaway

The perfect romantic get away / launch pad for local events. 2 private rooms, main bedroom, sitting room / bedroom, with full size sofa bed. Plus full bathroom, dual vanity & kitchenette. Enjoy a private deck, entry doors and parking steps away. Beautiful foliage in season, nearby lakes, state parks, snow shoeing, x country & down hill skiing. 15 minutes to UNH & 25 minutes to the seacoast. Located on a "scenic" road. Wonderful for long walks while you take in the beauty of New Hampshire.

17–24 Jun

$127 SGD per night
Guest favourite

Cottage in Northwood

4.91 out of 5 average rating, 214 reviews

Cottage near lake! Includes canoe! Dog friendly!

Come relax, sit by the fire pit, walk the dirt roads & trials! Walk 2 min. to the boat launch/swim area & enjoy the canoe. WIFI. 500 mbps. Yard: grill out, make s'mores by the fire pit, play horse shoes. Inside: play games, complete puzzles, cuddle up and watch movies. Outings: Antique Alley, Chucksters, Stonehouse Pond, Meadows State Park, Portsmouth,Concord. *Sleeps 4. *PET FEE $25 per dog/ night. 1-2 behaved dogs. Dogs only due to health concern for cleaner. *Wear life jackets provided.

28 Sep – 5 Oct

$202 SGD per night
Guest favourite

Loft in Barrington

4.96 out of 5 average rating, 489 reviews

Sunny, secluded studio loft apartment

Fully furnished studio apartment above home owners' garage with private entrance. Secluded 5.5 acre lot of land surrounded by beautiful woods. Vaulted ceilings with ladder to loft with queen bed. Big, sunny south-facing windows overlooking back yard and gardens. Homeowners are a laid-back, married gay couple, living in the main house with their 2 year old daughter and a dog. LGBTQ friendly home that welcomes kind guests of any race, religion, gender, and orientation. A minute from Route 125.

25 Aug – 1 Sep

$128 SGD per night

Popular amenities for Pittsfield holiday rentals

Stay near Pittsfield's top sights

Main Street Bar And Grill8 locals recommend
Chichester Country Store3 locals recommend
Appleview Orchard4 locals recommend

Other great holiday rentals in Pittsfield

Guest favourite

Cottage in Middleton

4.96 out of 5 average rating, 135 reviews

☀ Fox & Loon lake house: hot tub/pedal boat/kayaks

18–25 Oct

$474 SGD per night
Guest favourite

Cabin in Barnstead

4.95 out of 5 average rating, 164 reviews

Scenic Chalet: Hot Tub, Amazing Views, Near Skiing

5–12 Jun

$658 SGD per night
Guest favourite

Farm stay in Alton

4.99 out of 5 average rating, 298 reviews

Treehouse Penthouse ❤ Beautiful inside & out

19–26 Oct

$245 SGD per night
Guest favourite

Cottage in Alton

4.87 out of 5 average rating, 156 reviews

1 Bedroom Cottage w/Lake Winnipesaukee View/Access

3–10 Feb

$181 SGD per night
Guest favourite

Flat in Newmarket

4.96 out of 5 average rating, 196 reviews

Spacious private Studio & Experienced SuperHosts!

29 Apr – 6 May

$124 SGD per night
Guest favourite

Farm stay in Epsom

5.0 out of 5 average rating, 70 reviews

Antq. Farm Ell-Private deck/views/trails/Dog yard!

8–15 Feb

$215 SGD per night
Guest favourite

Cottage in Barrington

4.92 out of 5 average rating, 49 reviews

A little house in the woods

15–22 Nov

$143 SGD per night
Guest favourite

Home in Epsom

4.96 out of 5 average rating, 51 reviews

Waterfront Getaway Home in Epsom, NH

19–26 Dec

$388 SGD per night
Guest favourite

Home in Pittsfield

5.0 out of 5 average rating, 21 reviews

Restored Historic Colonial with Mountain Views

10–17 Apr

$1,232 SGD per night
Guest favourite

Home in Epsom

4.98 out of 5 average rating, 63 reviews

Lakefront-Dock-Grill-Firepit-Wood Stove

13–20 Oct

$500 SGD per night
Guest favourite

Guest house in Alton

5.0 out of 5 average rating, 7 reviews

River Run Cottage in Alton, NH

7–14 Sep

$209 SGD per night
Guest favourite

Flat in Alton

4.92 out of 5 average rating, 61 reviews

Downtown, Super Private & Cozy Loft Style Apt.

23–30 Aug

$170 SGD per night

Destinations to explore