Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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Top guest favorite
A spacious home sits on a manicured lot, featuring a well-kept garden and an expansive driveway. The two-story structure boasts large windows and a welcoming entrance, with outdoor lighting enhancing its features during twilight. The attached garages are visible on the right.
Guest suite in Windham
4.99 out of 5 average rating, 293 reviews

Sunny, private and peaceful apartment!

Our home sit in a private and peaceful setting. It is perfect for the business travelers looking for a place to relax at the end of the day or anyone looking for a quiet place. Close to Castleton Banquet and Conference Center, Searles Castle, Canobie Lake Park, walking & biking trails, shopping and restaurant. Centrally located between Boston, beaches and mountain and lake region. Only 16 miles from Manchester Boston Regional Airport, 36 miles from downtown Boston, 3.5 miles from Interstate 93.

Guest favorite
A welcoming sitting area features two comfortable chairs beside a small round table. Natural light floods through large windows, showcasing views of the serene lake. A television is mounted above a decorative fireplace, creating an inviting space for relaxation.
Home in Derry
4.92 out of 5 average rating, 508 reviews

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.

Top guest favorite
A modern kitchen area features stainless steel appliances, including a refrigerator and a gas stove. Open shelving displays decorative items. A dining table and chairs are situated near the room's entrance, while a doorway leads to a bathroom in the distance.
Apartment in Derry
4.95 out of 5 average rating, 80 reviews

Gorgeous Lakefront Suite Apartment (Unit 3)

Get away to a lakefront retreat in beautiful southern NH! Enjoy our 1 bedroom unit that is part of a gorgeous 3 family waterfront home. This suite comes complete with a thoughtfully decorated living room, a stocked kitchen, and furnished with a queen-sized bed and an air mattress upon request. Enjoy free shared lake access! It is 8 minutes from I-93 and a short drive to Canobie Lake Park, Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White Mountains.

Top guest favorite
A blue two-story house is surrounded by lush greenery, providing a serene backdrop. The front features large windows, a staircase leading to the entrance, and a spacious driveway with ample parking. Attached garage doors are visible on the right side.
Guest suite in Hampstead
5 out of 5 average rating, 22 reviews

Lakeview Ste./Wineries/Golf/Fall Attractions/KgBd

Escape to your private cozy suite—perfect for a romantic getaway, solo retreat, or a peaceful work trip. Nestled in the heart of Southern NH, this haven blends comfort with nature. Unwind on a plush King-sized mattress while the soothing sounds of loons lull you to sleep. Start your day with a cup of coffee or a quick meal, then explore nearby beaches or scenic spots. Whether you're relaxing or adventuring, this suite offers the perfect balance of convenience and tranquility. Your escape awaits!

Superhost
The exterior of The Word Barn is illuminated against a twilight sky, showcasing its distinct architectural features. Warm lights line the entrance, and large windows reveal a welcoming interior. Surrounding greenery adds to the tranquil ambiance of the private setting.
Barn in Exeter
4.87 out of 5 average rating, 554 reviews

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.

Top guest favorite
A spacious living area features a gray sofa and a patterned armchair, accompanied by a wooden coffee table. A small table holds a lamp and magazines. A doorway leads to the bedroom, while a kitchenette is visible in the background.
Guest suite in Merrimack
4.99 out of 5 average rating, 265 reviews

Guest suite with king bed and private entrance

Come and relax in our spacious one-bedroom basement guest suite that is comfortable and bright. It has a private entrance with off street parking. The suite has a large living area, bedroom with king bed and private bath . The location is an ideal 20 minutes from the Manchester/Boston Regional airport and 10 minutes from the Merrimack Premium Outlets as well as a wide variety of restaurants. Boston, skiing, the beach and the #1 most hiked mountain in the world are all about an hour away.

Guest favorite
Guest suite in Merrimack
4.85 out of 5 average rating, 54 reviews

Pet/Kid Friendly Travel Nurse Studio Apartment

Kid and Pet Friendly! Cozy basement apartment in a quiet neighborhood in southern New Hampshire. Located 50 minutes from Boston airport, 1.5 hours from the White Mountains, and 1 hour from the beach it’s a perfect location to take in all of New England! COVID free home with extra sanitizing precautions and sterilizing all surfaces between guests. Close to Nashua and Manchester with easy commutes to Boston, Concord, or Portsmouth! Pets and kids welcome. Toddler and infant beds available.

Top guest favorite
The studio features a spacious bed with white linens, accented by decorative throw pillows. A vibrant piece of art adorns the wall above the bed. A modern vanity area with a sink is visible, along with natural light filtering through windows that offer views of the surrounding woods.
Guest suite in Milford
5 out of 5 average rating, 149 reviews

New England Village Luxury Studio

Kick back and relax in this stylish studio! Our house is in a quiet neighborhood of older homes surrounded by woodlands yet conveniently located downtown, a half mile from our village green (Milford Oval). A short stroll over the river will take you to cafes, restaurants, pubs with live music, post office, library, shops & useful stores such as CVS. Whatever brings you…business, skiing, hiking, antiques, a family celebration or a romantic weekend away…we are looking forward to hosting you!

Guest favorite
A modern kitchen is presented, featuring dark wooden cabinets and a central island. A stainless steel refrigerator and microwave are visible, while a small dining table with black chairs occupies one corner. Light-colored tile flooring enhances the spacious feel of the area.
Home in Hanover Hill
4.89 out of 5 average rating, 19 reviews

Pet-Friendly 2BR| Parking+Laundry | Prime Location

Welcome to your home away from home in Manchester! This cozy, first-floor apartment offers two bedrooms, a full bath, and space to comfortably accommodate up to four guests. Enjoy the ease of driveway parking for 1 car, in-unit laundry, and no stairs—perfect for families, professionals, or anyone looking for a relaxed, accessible stay. We’re pet-friendly, so bring your furry friends! Centrally located— quick access to dining, hospitals, downtown, and more. We look forward to hosting you!

Superhost
A cozy living area features a light-colored sofa adorned with plush throw pillows. Natural light floods in through large windows, illuminating the space. A tabletop and decorative plant are visible in the background, adding a touch of warmth to the inviting ambiance.
Apartment in Derry
4.76 out of 5 average rating, 399 reviews

Downtown Derry, Studio Apartment

Cozy up during your next trip to southern NH! Built in 1910, the home has been completely renovated. The Studio is a combination of elegance and comfort from the walls of windows that flood the space with light and scenic conservation/golf course views to the spacious backyard that is perfect for a peaceful escape. It is 5 minutes from i-93 and a short drive to Canobie Lake Park, Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White mountains.

Superhost
The master bedroom features a spacious bed adorned with textured bedding and decorative throw pillows. A macramé wall hanging adds visual interest above the bed, and a softly lit lamp provides gentle illumination, creating a serene environment.
Apartment in Manchester
4.91 out of 5 average rating, 35 reviews

Cozy Central Downtown 2BD Unit Close to 93 & Elm

Enjoy this stylish space at this centrally located apartment right in downtown Manchester, designed for you and your family to relax, and enjoy what New Hampshire has to offer. We designed this space to accommodate your everyday needs as well as please the eye. Located on a very busy/noisy street. ✓ 2 Mins to downtown Elm Street ✓ 3 Mins to Interstate 93 ✓ 5 Mins to the Elliott Hospital ✓ Tons of things to do/eat close-by ✓ Free on-site parking ✓ Easily Accessible ✓ Private Entrance

Guest favorite
A cozy bedroom features a wooden bed frame with a layered blanket on a spacious bed. A light streams through a window adorned with soft curtains, illuminating the room. A leather chair sits in the corner, adding to the welcoming atmosphere.
Guesthouse in Londonderry
4.9 out of 5 average rating, 30 reviews

The Sweet Suite - Close 2 MHT+93

Come and stay at the Sweet Suite, a hidden gem in Londonderry, NH perfect for a weekend getaway or a traveling worker. This apartment features a sleep number bed for restful comfortable nights as well as a full eat in kitchen and living room area. Perfectly situated just 5 minutes from 93 and 15 minutes from MHT airport (We checked!). This property is well suited for commuters or for those looking to explore the great natural wonders NH has to offer. Families also welcome!

Popular amenities for Chester vacation rentals