
Vacation rentals in Chester
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Chester
Guests agree: these stays are highly rated for location, cleanliness, and more.

Peaceful Mill with Waterfall - Home Away From Home
Immerse in tranquility at our serene mill retreat in Southern NH. This historic space, adorned with original timber, rustic brickwork, and lofty 11 ft ceilings, offers a spacious 2,650 sq ft sanctuary. Relax in the soaking tub, or savor the calming waterfall views from the deck. Conveniently near downtown, but distant enough for undisturbed peace. Welcome to your soothing retreat for rest and rejuvenation. A remote worker's dream office with high speed connectivity and dedicated remote workspace

Luxury Year-round Treehouse with private hot tub
Cliff House is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Little Lake House, the Bungalow
Cozy up during your next trip to southern New Hampshire! The Little Lake house, situated right next to a serene lake, boasted luxury and spectacular water views. It's a perfect place for a peaceful escape or chance to experience the wide variety of seasonal New England activities from swimming and leaf peeping to ice fishing. The Little Lake house is a short drive to Canobie Lake Park and Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White mountains.

The Word Barn, Exeter, NH
Charming open apartment with a loft bedroom. Hardwood floors, barn beams, butcher block counter, full galley kitchen, private bath, vaulted ceilings - as part of the renovated original Raynes Farm Barn. This apartment is clean, private and isolated, with self check-in and plenty of outside space to enjoy. Located five minutes from downtown Exeter (w/plenty of take-out/delivery options) in an idyllic country setting, neighboring 100+ acre conservation land and a large network of wooded trails.

One Level 2 bedroom suite on private cul-de-sac
Welcome to The Sama's Airbnb. Windham was recently named the #1 town in the Granite State. Here, you will enjoy a complete newly renovated private one level 2 bedroom suite complete with full kitchen, cozy living room, 40 inch LED TV with all channels, wifi, washer and dryer, new tennis court, 1/2 basketball court and pickleball, beautifully landscaped grounds on a private cul de sac yet close to Boston, beaches, mountains, shopping, great restaurants, Searles Castle, Canobie, & Tuscan Village.

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

Haven by the Lake
Looking for a place to bring the family, or a get-a-away with friends? This is it! From the light and airy design that makes it feel like home to the hot tub, loft room, and lake access, The Haven by the Lake has everything you need for a great stay. It is a short 100 yard walk from the lake and a quick drive to Canobie Lake Park and Manchester Airport, 45 minutes to Boston or the NH Seacoast, close to the Lakes Region, White mountains, and great skiing spots as well as the famous NH Outlets.

The Raven!
Looking for the quintessential Salem stay? Look no further! The main bedroom is designed to get you in the Salem spirit, with its dark gothic decor. Take a reading break in the adjacent room, outfitted to look like a Victorian British library. A spacious living room, dining room, kitchen, and full bath complete this lovely property. Enjoy parking in a driveway in the typically-packed city. We are just a quick and enjoyable 12-minute walk to Essex street and all that downtown has to offer!

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.

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.

Little Lake House- Swimming, Fishing, Waterfront
Welcome to our home away from home. This cozy lake get away just minutes over the border from Massachusetts is the perfect place to connect with friends and family. Enjoy days out on the water which is right outside your back door! Or nights at the fire pit enjoying the stars. We have wifi, tv w/ streaming services, laundry, a/c & heat, and kayaks to make your stay as comfortable and fun as possible. We're family friendly and have a crib for infant/baby.

Bright & Sunny Studio
This newly remodeled, bright and sunny studio will not disappoint, located just off the highway, near Manchester, NH, a short drive from downtown. Brand new, very clean studio apartment with a private entrance, private bathroom, kitchen, lots of windows, and work space. Outside your windows, there is a small orchard for you to enjoy during harvest seasons. SNHU: 1mile Downtown Manchester: 5min Concord: 20min 1 hour from Boston or White Mountains
Popular amenities for Chester vacation rentals
Other great vacation rentals in Chester

Amazing House, Peaceful Shangri-La w/Pool &Hot-Tub

Perfection on Pleasant Lake

Quaint mountain top Bungalow

Private Waterfront home

Loon's Ledge Lakehouse

Cabin Fever

Charming New England Farmhouse

Secluded Estate Home w/ Indoor & Outdoor Amenities
Destinations to explore
- Plainview Vacation rentals
- New York City Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- Québec City Vacation rentals
- Hampton Beach
- Fenway Park
- TD Garden
- Harvard University
- Boston Common
- Ogunquit Beach
- Wells Beach
- New England Aquarium
- Revere Beach
- Boston Seaport
- Boston University
- Northeastern University
- Weirs Beach
- Freedom Trail
- Boston Convention and Exhibition Center
- MIT Museum
- Pats Peak Ski Area
- Long Sands Beach
- Monadnock State Park
- Canobie Lake Park
- Crane Beach
- Quincy Market
- York Harbor Beach
- Museum of Fine Arts




