Vacation rentals in Pittsfield

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Top-rated vacation rentals in Pittsfield

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Top guest favorite
A modern cabin with an A-frame shape is illuminated by warm lights, surrounded by tall trees. In front, a fire pit with wooden chairs invites gatherings, while a hot tub and sauna are visible nearby, contributing to the outdoor relaxation space.
Cabin in South Berwick
5 out of 5 average rating, 287 reviews

Romantic A-Frame cabin in the woods

Stay at Hidden Pines Cabins. Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

Top guest favorite
A charming red farmstead is set against a snowy landscape, showcasing a classic sloped roof and warm lights glowing from its windows. A fenced yard and a snow-covered driveway lead to the entrance, while snow-dusted trees surround the property.
Farm stay in Epsom
4.97 out of 5 average rating, 128 reviews

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

This farmstead "ELL" has 1800's character, yet updated for modern day. WiFi & AC! We hope this space inspires. Orig. hand hewn beams, pine floors, woodstove & vntg. bath tub to warm you after a day skiing or family sliding down threw the fields. Mtn. bike or walk the trails. Prvt. deck w/grill, fenced yard, firepit & views. We are here all 4 seasons @ "Windy Ridge Inn" Nh snowmobile trails at your door! UNH, Dell Lea, Gunstock Mt, Laconia, Atlantic Ocean, NH lakes, ME Outlets. 90 min to Boston

Top guest favorite
A vibrant blue cottage sits nestled among greenery, with a welcoming entrance and an American flag displayed. A dock with two kayaks rests at the water's edge, reflecting the serene lake. A patio area is visible on the upper deck, inviting relaxation.
Cottage in Northwood
4.94 out of 5 average rating, 133 reviews

Cottage on the lake! Includes kayaks & rowboat!

Super cozy, beautiful cottage right on the lake & dirt roads. Yard: sitting areas, propane fire pit, fenced in yard. Inside includes reading areas, dvds, wifi, books, coloring books, puzzles, games. Enjoy the rowboat & kayaks or bring your own boat. We are on Antique Ally and State Parks are nearby (2 miles away). Enjoy a day at Chucksters, Concord, Portsmouth or the lakes region. Enjoy the LAKE LIFE! No animals (Health concern for cleaner) 4 adults or 2 adults 3 kids. Life jackets provided

Top guest favorite
Guesthouse in Alton
4.99 out of 5 average rating, 478 reviews

The Vineyard Penthouse - Beautiful Inside & Out

Wake up to rows of sun-kissed grapevines and unwind in a serene, vineyard-view retreat. This open-concept suite featured a plush king bed, abundant natural light and inviting modern décor. Sip wine at sunset, cook in the well-equipped kitchen, or unwind and relax, in our new “shared” hot tub. Although there are other guest on the property you will have this space to call your own and enjoy. ~ 5 min from Lake Winnipesukee, 20 min to Wolfeboro, 20 min to Gunstock and 25 min to Bank of Pavilion

Top guest favorite
The living area features a combination of seating, including a couch and armchair, positioned near windows that allow natural light. A small dining table with checkered fabric sits adjacent, while framed artwork adorns the walls, adding character to the space.
Apartment in Lee
4.93 out of 5 average rating, 171 reviews

In the country but near the action.

One-bedroom apartment. Separate entrance and dedicated parking. No charge for well behaved children and pets. In Rural NH on 7.5 acres. Enjoy our large yard, porch, patio, flower garden, gas grill and nature trail in our private woods. Near Portsmouth and the NH seacoast, one hour from Boston, Portland, Me, and the White Mountains. Four miles from Univ. of New Hampshire. Secure Wi-Fi TP-Link 6E mesh router, Hi-Fi, DVD's and 2 smart TV's. We treat our guests as guests. LGBTQ+ welcome. .

Guest favorite
A tranquil fire pit area is set up with several wooden chairs arranged in a circle, illuminated by a warm glow from the fire. The surrounding darkness is contrasted by the soft light, creating a cozy atmosphere amidst tall trees and a distant night sky.
Guesthouse in Kingston
4.99 out of 5 average rating, 127 reviews

Accessory Apt on Wooded Property

Forget your worries in this spacious and serene space. Guest House/Over Garage Apartment tucked away on 6 acres. Centrally locataed in the seacoast region of New Hampshire. Close to mountains, beaches, hiking trails, lakes, & more. 15 minutes to Exeter, 30 minutes to North Hampton/Hampton Beach, 35 minutes to Southern Maine and Portsmouth, NH, 40 minutes to Manchester Boston Regional Airport, and 1 hour to Downtown Boston yet still tucked away in your own private retreat in the woods.

Top guest favorite
A cozy outdoor seating area features two wooden chairs arranged around a circular stone fire pit. The space is surrounded by landscaped mulch and bordered by a winding pathway. Lush greenery and a home can be seen in the background, contributing to a serene atmosphere.
Loft in Barrington
4.96 out of 5 average rating, 561 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 5 year old daughter. LGBTQ friendly home that welcomes kind guests of any race, religion, gender, and orientation. A minute from Route 125.

Top guest favorite
A serene lakeside view is presented, featuring a well-maintained garden with colorful flowers and lush greenery. Smooth stones create a path leading towards the calm waters of Sunrise Lake. The dock and surrounding trees are visible under a bright blue sky with scattered clouds.
Cottage in Middleton
4.96 out of 5 average rating, 222 reviews

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

Escape to a peaceful, lakeside retreat with a secluded sun-lit deck and private dock with incredible views of Sunrise Lake, plus a 4-person hot tub, and seasonal amenities like a pedal boat, two kayaks, a SUP board, gas fire table, central A/C, a pellet stove, and snowshoes. Enjoy nearby activities like hiking, leaf peeping, skiing, and visiting scenic towns, local vineyards and breweries — or simply relaxing in a beautiful lakefront setting. The sunsets can be unbelievable!

Top guest favorite
A serene lakeside view is presented, featuring a wooden dock extending over the water. Lush green trees line the shore, with a flower garden in the foreground. A small decorative figure sitting near the water adds charm to the landscape, enhancing the peaceful atmosphere.
Cabin in Nottingham
4.99 out of 5 average rating, 186 reviews

Rustic Log Cabin on Pawtuckaway Lake

Our Cabin is located on Pawtuckaway Lake in Nottingham, NH where there is year round enjoyment! This is an older cabin built in 1970, with rounded logs and lots of warmth and charm. There is a beach area for swimming, patio for hanging out enjoying the views with a firepit as well as a dock for sunbathing and fishing. There is a public boat launch on the lake if you want to bring your own boat. Close to Pawtuckaway state park for hiking and mountain biking.

Top guest favorite
A wooden interior features a cozy seating area with a plaid sofa and two upholstered chairs. A round dining table surrounded by four chairs offers a warm spot for meals. Bookshelves line the wall, providing a collection of reading materials.
Apartment in Loudon
4.91 out of 5 average rating, 636 reviews

A - Farmhouse Apartment on a Cattle Farm

The apartment has a full private kitchen with a dishwasher. Breakfast is not provided. There is a one-time pet cleaning fee. We allow pets, but if you plan to leave your pet unattended in the apartment, dogs and cats must stay in an appropriate crate. We reserve the right to enter the apartment if an unattended pet is noisy or is not in a crate. The bathroom tub's bubbling jets do not work.

Guest favorite
A cozy bedroom features a spacious bed adorned with a patterned blanket, flanked by two black nightstands. Nature-inspired wall art displays mountains and trees, complemented by plaid curtains. A vibrant area rug adds warmth to the wood flooring, creating a welcoming atmosphere.
Cottage in Gilford
4.87 out of 5 average rating, 220 reviews

A: Summer, Lake, Ski, Hike, Concerts

Gilford, Fully furnished one bedroom HOUSE!! Dog Friendly, (with host permission) for one dog. has a fenced and gated yard and a fire pit. Super Cute! updated, nice area, off street parking, private fenced yard. WIFI, Roku TV, Kitchen with all utensils, coffee maker, coffee, filters, sugar, Linens. .Close to great restaurants and attractions, lake, hiking. skiiing, zip lines concerts!

Guest favorite
A serene bedroom setting features a spacious bed with white bedding. Flanking the bed are two bedside lamps with soft light. A mountain landscape painting hangs above, complemented by built-in shelves holding books and decorative items, showcasing a cozy and inviting ambiance.
Guest suite in Concord
4.96 out of 5 average rating, 273 reviews

Bright ‘n Cozy Cottage in Concord

The Cottage is attached to our 1880 New Englander. We live right next door to the Cottage with our two pups. You will have the entire guest suite to yourself. Enter through the door off of the deck. The kitchen and living room are on the first floor and the bathroom is located between the first and second floors. One bedroom has a full-size mattress and the other has two twin beds.

Popular amenities for Pittsfield vacation rentals