Vacation rentals in Oxford

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Oxford

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

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Top guest favorite

A charming house with a mix of stone and siding is presented, surrounded by lush greenery and trees. The two-story structure features a prominent stone chimney. A pathway leads from the front yard, creating a welcoming entrance to this serene setting.

Home in Brookfield

4.98 out of 5 average rating, 148 reviews

Stay at Old Dorset Farm & create lifelong memories

This 1905 Historic Old Bakery is the perfect location to create lifelong memories while exploring quaint New England. Set on 4 acres, with a lake, trails and golden rolling hills just minutes away, you’ll enjoy all of New England's beauty. Hiking, kayaking, antiques shopping or gallery visiting... it can all be done right here. But you don't have to go anywhere. The two fireplaces invite you to just stay, relax and enjoy the complimentary bottle of Prosecco. Follow us on Insta: @Old_Dorset_Farm

Superhost

A clean, modern bathroom is showcased, featuring light wood paneling. A small sink with a mirror above is situated beside a toilet. Fresh towels are neatly hung on a rack, and a door leads to a private shower area, enhancing convenience.

Guest suite in Ansonia

4.73 out of 5 average rating, 494 reviews

Private Inn

Private(not shared) self check-in, clean, quiet, safe, and free off street parking on a cul de sac road. The suite is 600sq your own private bathroom, backyard, and number keypad for your convenience to enter/exit into the suite at will, there is high speed Wi-Fi, HD cable tv, Kcup machine, heat/ac (indoor fireplace) also a firepit outsde ,rubber track and tennis courts literally in the back yard. 5miles away from Yale/nh and 5mins to Griffen Hospital and major highways great local restaurants

Guest favorite

A covered outdoor seating area features a combination of woven chairs and a sofa arranged around a stone floor. Soft lighting is provided by string lights overhead, while rustic wooden beams and walls create a warm, inviting backdrop.

Guesthouse in Southbury

4.94 out of 5 average rating, 324 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Top guest favorite

Apartment in Southbury

5 out of 5 average rating, 25 reviews

New Apartment Centrally Located in Southbury

Keep it simple at this peaceful and centrally-located apartment. Recently renovated with all the essential amenities to make your stay just like home. Wi-Fi, washer, dryer, cooktop, fridge, oven, microwave, toaster, smart TV and Keurig are ready to make your stay pleasant. An outdoor porch is available for dining in warmer months. It includes one new queen bed plus sofa bed for one adult or two kids. Located just minutes from shopping and dining in downtown Southbury with easy access to 84

Guest favorite

The bathroom features warm orange walls and a tiled floor. A white toilet is positioned against one wall, with a mounted toilet paper holder nearby. Two dark wooden shelves are installed above a sleek countertop, providing space for toiletries or storage.

Guest suite in Watertown

4.91 out of 5 average rating, 196 reviews

Lrg Studio Apartment - walk to Taft

Welcome to my downstairs space! This clean open concept space is ready for your long term or overnight stay. This studio space is the lower level of a raised ranch house. I live upstairs with my dog and share laundry with airbnb guests. The space has a private entrance through the garage, private bath, and kitchen area in a quiet neighborhood. Walking distance to Taft and convenient to Rts 8 & 84. Off street pkg. Whether you are interested in two nights or two months, you are welcome here!

Top guest favorite

A functional laundry area is showcased, featuring a washer and dryer side by side. The space is well-organized, with a metal shelving unit positioned above, storing cleaning supplies. Exposed utility lines and concrete walls provide a utilitarian background, contributing to the overall practicality of the area.

Apartment in Milford

4.98 out of 5 average rating, 105 reviews

The Pond Mill Retreat w/ 2 Bdrms & Pool

Catch up on a little work or simply unwind. Everything is waiting for you in this cozy, yet functional space surrounded by a beautiful wooded area with pond. Your private entrance accommodations include a finished, walk-out lower-level apartment (~730 sq ft) containing thoughtfully appointed bedrooms, living room, kitchen, and full bathroom. Experience solitude while enjoying the convenience to Rt 15, I-95, & Boston Post Rd destinations. And if you require assistance, we live right upstairs.

Guest favorite

A Keurig coffee maker sits on a kitchen countertop next to a clear electric kettle. A variety of coffee pods is displayed on a carousel nearby. A large white cup rests on the base of the Keurig, while cream and sugar options are placed in a small dish.

Cottage in Seymour

4.93 out of 5 average rating, 56 reviews

3 Acre Forest, 2 King Beds, Fireplace, BBQ & more

🛏️2 king, 2 twin, BBQ, fireplace, firepit, 1550 sqft entire house 🅿️🛜 Tucked away at the end of a quiet street, set on 3+ acres of lush wooded land, our home is the perfect blend of seclusion and convenience. With a forest as your backyard and RT34 one min away, you can easily balance your desire for nature and adventure with the need for easy travel and commuting, take a short hike into a forest (trails minutes away) and/or relax under the stars around a fire pit.

Guest favorite

A rustic game room features wooden walls with a rich texture, complemented by a pool table at the center. A long table lined with benches offers seating, while various artworks are displayed on the walls. Soft lighting adds to the inviting ambiance.

Apartment in Brookfield

4.92 out of 5 average rating, 282 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Guest favorite

A rustic stone building features large windows and a welcoming porch area with seating. Bright flowers and greenery surround the entrance, while a large umbrella provides shade over the outdoor seating. The building's design harmonizes with the natural surroundings.

Cabin in Newtown

4.89 out of 5 average rating, 117 reviews

Sticks and Stones Farm - The Solar Cabin

Sticks and Stones Farm offers a rustic glamping experience! When you stay with us you'll get the adventure and fun of camping (no electricity, outdoor showers etc.) while still getting to lay your head on a soft pillow in a bed. You can treat your stay here as a chance to go inward or enjoy interacting with the different programs and events going on! If you want to be up to date on events or ask about weekday checkins you can message us directly.

Top guest favorite

A small outdoor patio area features a round glass table surrounded by two black wicker chairs. The space overlooks a grassy area with lush trees in the background, creating a serene environment for outdoor relaxation.

Home in Southbury

4.99 out of 5 average rating, 121 reviews

The Cottage at Cedar Spring Farm

Welcome to The Cottage at Cedar Spring Farm located on a 16 acre working (in progress) farm bordered by 155 acres of protected land trust with marked hiking trails. Southford Falls and Kettletown State Park are within minutes for fishing, picnicking, and hiking. Conveniently located to I-84, shopping, local farms, wineries, breweries, restaurants, and Heritage Village. Please note that we allow pets (dogs only) and have a limit of two.

Top guest favorite

A spacious outdoor patio features a mix of seating options including lounge chairs, a sofa, and several tables. A shaded area is provided by an umbrella, and landscaped greenery surrounds the space. A greenhouse is visible, adding to the serene setting.

Guest suite in Woodbridge

4.92 out of 5 average rating, 153 reviews

Cupola Hill -a 2 BR guest suite with bucolic views

Beautiful 2 bedroom guest suite attached to main house with separate entrance, bathroom, living room. Set on magnificent 20 acre estate, perfect country get away, only 15 minutes to Yale and downtown New Haven. It’s the best of both worlds! Come enjoy the great restaurants of New Haven and then head to Cupola Hill for an evening in the country! Have a glass of wine under the stars and watch the wildlife!

Top guest favorite

A lush garden space is surrounded by vibrant greenery and flowering plants. A brick patio features a red umbrella over a small table and chairs, providing a shaded area for relaxation. Decorative planters enhance the tranquil setting, inviting guests to enjoy the outdoors.

Guest suite in Wallingford

5 out of 5 average rating, 592 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station.

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Popular amenities for Oxford vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Oxford

Guest favorite

A functional kitchen area features wooden cabinetry, a stainless steel oven, and a microwave. Countertop appliances include a coffee maker and toaster, while a decorative towel hangs from the stove. A light-toned backsplash complements the warm wood tones and dark flooring.

Guest suite in Waterbury

4.91 out of 5 average rating, 119 reviews

Private cozy getaway

WalterRating, 5 stars2 weeks ago

Lovely place. Nice large shower, plenty of space.

Superhost

The private entry features a dark door with an arched window, framed by white curtains that softly billow in the breeze. A small seating area is visible to the side, with a decorative metal stove positioned nearby, creating an inviting outdoor space.

Vacation home in Woodbury

4.83 out of 5 average rating, 24 reviews

UNIQUE and GORGEOUS historic loft style rental

EmilyRating, 5 stars1 month ago

What a lovely homebase for a quick trip to see some pals near my old town. Beautifully clean and cozy, slept like a brick, and the space is so charming and cozy while still having everything one could need.

Superhost

A bear is seen crossing a quiet, tree-lined road. Green foliage surrounds the area, and a stop sign stands nearby, indicating the presence of a residential or rural setting. Sunlight filters through the leaves, creating a soft illumination of the scene.

Home in Watertown

4.8 out of 5 average rating, 44 reviews

Cozy Cottage

KatieRating, 5 stars3 weeks ago

This was the perfect place to relax after visiting family all day. Hector's place was clean, private, and peaceful. the drive way is a little hard to find but GPS will get you there fine. The airbnb had everything we needed and loved the back deck for grilling. highly recommend.

Guest favorite

Home in Newtown

4.97 out of 5 average rating, 160 reviews

Spacious, private home, must see!

RachelRating, 5 stars3 weeks ago

The home is much bigger than expected! Very comfortable and lots of natural light. Checkin was very easy. Norm came by to make sure we were allset and was incredibly friendly. We were traveling with an infant and he gave us a pack & play and high chair which was incredibly helpful & thoughtful! The location is very private and quiet which felt very safe with a baby. But you are still so close to downtown! We recommended the listing to our family who visit the area often. We would definitely stay again!

Guest favorite

A fire pit is constructed from a circular arrangement of large, natural stones, with a small stack of firewood positioned centrally. Surrounding grass is well-maintained, providing a spacious outdoor area for relaxation. Dense greenery and trees form a serene backdrop.

Guest suite in Newtown

4.95 out of 5 average rating, 95 reviews

Light and airy, pet friendly rental in Newtown

DawnRating, 5 stars1 week ago

Suzanne’s place was spotless! I stayed here one night with two of my daughters and we were very comfortable. We got in later than expected, from a family graduation, and Suzanne was very kind and quick in responding. Her place is in a quiet, peaceful neighborhood. We also liked her local guide and went to Caraluzzi’s market for groceries. Thanks for a great stay!

Guest favorite

A sunroom features a dining area with wooden chairs around a large table and two upholstered chairs with white cushions. Natural light fills the space through large windows, and a fan is mounted on the ceiling. A small side table sits beside one of the chairs.

Home in Newtown

4.97 out of 5 average rating, 65 reviews

Charming Relaxing Raised Ranch

JeffRating, 5 stars3 weeks ago

Incredibly clean, well stocked, private, and in the perfect location. You can enjoy the home with its large back yard and beautiful sunroom, or go walk to the restaurants that are right around the corner. Beth’s place has everything for a perfect stay. 1000% recommend staying here.

Top guest favorite

A view seen through open French doors showcases a grassy area leading to a serene pond. The landscape includes a nearby building and trees, while a few potted flowers sit on the edge of the stone steps.

Home in Watertown

4.96 out of 5 average rating, 26 reviews

Carriage House on Smith Pond!

BetsyRating, 5 stars6 days ago

By far one of the nicest air B&B’s we’ve stayed in. Beautifully renovated carriage house on an incredible piece of property. Todd and Janet warmly welcomed us with their chickens’ fresh eggs, fruit and muffins. Kitchen was well equipped for preparing meals and we enjoyed dining al fresco while hawks flew and deer ran across the fields. Upstairs is a comfortable bed with nice linens and a large bathroom. This is a real gem! We hope to return in the future.

Top guest favorite