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Vacation Homes in Pittsfield

Perfect Modern Lake Front Retreat with Dock! Sleeps 4

9.6 out of 10, Exceptional, (19)
"The place was quaint, modern and lovely. The views were fabulous! "
The price is AED 951
AED 1,521 total
includes taxes & fees
17 Jul - 18 Jul
Perfect Modern Lake Front Retreat with Dock! Sleeps 4

Lakefront Home with Private Beach Access & Hot Tub

10.0 out of 10, Exceptional, (6)
"Alex was very helpful, constantly checking in. House was equipped with everything you may need. He even let us check in an hour early. Great spot to stay."
Lakefront Home with Private Beach Access & Hot Tub

The Cottages at Harvey Lake

3.0 star property
8.6 out of 10, Excellent, (44)
"The view of the lake from the cabin was excellent. "
The price is AED 558
AED 606 total
includes taxes & fees
21 Jul - 22 Jul
The Cottages at Harvey Lake

Safe Peaceful Quite Bright Gorgeous Accessibility

7.8 out of 10, Good, (9)
Safe Peaceful Quite Bright Gorgeous Accessibility

Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock

9.8 out of 10, Exceptional, (27)
"Very peaceful spot, we had everything we needed."
The price is AED 1,697
AED 3,196 total
includes taxes & fees
15 Aug - 16 Aug
Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock

Lakeside Serenity! 3BR/2B Lake Front Retreat with Stunning Views

10.0 out of 10, Exceptional, (5)
The price is AED 1,102
AED 2,048 total
includes taxes & fees
23 Jul - 24 Jul
Lakeside Serenity! 3BR/2B Lake Front Retreat with Stunning Views

The Village of Paugus Bay Studio Close To It All!

8.8 out of 10, Excellent, (3)
"Place looked just like the pictures. Owner was responsive"
The price is AED 451
AED 912 total
includes taxes & fees
30 Jul - 31 Jul
The Village of Paugus Bay Studio Close To It All!

Idyllic Mountain and Lake Getaway

10.0 out of 10, Exceptional, (62)
"Absolutely gorgeous home and property nestled in the Gilford woods! Pristine and clean with every amenity needed. "
The price is AED 1,653
AED 3,188 total
includes taxes & fees
21 Jul - 22 Jul
Idyllic Mountain and Lake Getaway

Serene getaway with private sauna, firepit, deck, grill, balcony, & washer/dryer

8.4 out of 10, Very Good, (21)
"Amazing house for a family! Good layout and nice little yard with swings to play in."
Serene getaway with private sauna, firepit, deck, grill, balcony, & washer/dryer

Sunset-Facing Cottage on Mendums Pond in Barrington, NH

10.0 out of 10, Exceptional, (52)
"Beautiful setting on a quiet lake with loons and herons. We loved the deck overlooking the lake, and the kayaks and canoe provided (be sure to bring your own life vests)! The water was lovely and warm during our end-of-June stay."
Sunset-Facing Cottage on Mendums Pond in Barrington, NH

Spacious Lake View Laconia Apt Near Weirs Beach\ Pool \ Restaurants

The price is AED 401
AED 901 total
includes taxes & fees
6 Aug - 7 Aug
Spacious Lake View Laconia Apt Near Weirs Beach\ Pool \ Restaurants

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

10.0 out of 10, Exceptional, (174)
"Fantastic stay! The house was spotless, beautifully decorated, and had all the amenities we needed for a comfortable stay. The location was perfect—close to everything yet peaceful and relaxing. The host was responsive and made the check-in process seamless. Highly recommend and would definitely stay again!"
The price is AED 5,796
AED 10,354 total
includes taxes & fees
17 Jul - 18 Jul
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

Dog-friendly home with beach access, washer/dryer, gas grill, streaming services

8.2 out of 10, Very Good, (17)
"Everything was clean, organize and had plenty of everything we needed in kitchen, bathroom, etc. Thank you for making our stay for our sons wedding an enjoyable one."
Dog-friendly home with beach access, washer/dryer, gas grill, streaming services

Winnisquam Lake Retreat | House in Tilton with lakefront yard and gas grill

9.8 out of 10, Exceptional, (7)
"The property is charming, the direct lake access is fantastic, and the house is massive. Close to lots of shops and some really good seafood as well. Highly recommend."
Winnisquam Lake Retreat | House in Tilton with lakefront yard and gas grill

Waterfront home with wraparound deck, floating fireplace, deck, & firepit

6.8 out of 10, (27)
"Just did a little getaway with some friends place was super cute and clean cute little area. Will definitely be booking for the summer."
Waterfront home with wraparound deck, floating fireplace, deck, & firepit

Reuben Dimond House, Renovated Historic Farmhouse in the Capital, Concord, NH.

10.0 out of 10, Exceptional, (67)
"Quiet and comfortable. Great place to relax. "
Reuben Dimond House, Renovated Historic Farmhouse in the Capital, Concord, NH.

Lake-view townhome with lakefront swimming, pools, fireplace, tennis/pickleball

8.4 out of 10, Very Good, (12)
"We had an amazing time with our 2 kids. Ton to do in the complex and the unit itself was perfect!"
Lake-view townhome with lakefront swimming, pools, fireplace, tennis/pickleball

Terrific studio suite right on the water w/free WiFi, bay views, kitchenette

8.8 out of 10, Excellent, (5)
"I loved that it was one the lake with private beach access!! The room could be better with a bigger bed not so hard."
The price is AED 474
AED 1,036 total
includes taxes & fees
20 Jul - 21 Jul
Terrific studio suite right on the water w/free WiFi, bay views, kitchenette

Comfortable House w/ Private Gym + back Deck

10.0 out of 10, Exceptional, (1)
"What an amazing new house with everything you could ask for in a rental! Cant wait to go back"
Comfortable House w/ Private Gym + back Deck

The Coziest Tiny Home with Mini Cows & Horses!

9.6 out of 10, Exceptional, (13)
"Great sleeping!!!"
The Coziest Tiny Home with Mini Cows & Horses!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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