Holiday rentals in Roxbury

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Top-rated holiday rentals in Roxbury

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

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Guest favourite

Barn in Roxbury

5.0 out of 5 average rating, 15 reviews

Classic Red Barn with game room

Enjoy a fun and romantic stay in this renovated classic red barn on a private country property. The barn is only available when the main house is unoccupied, so you will have the whole barn, with game and fitness rooms, and the full run of the beautiful private country exterior property. If you're lucky, you'll get a visit from the horses at the neighboring horse farm! The barn's game room has a couch, ping pong and pool tables, basketball hoop outside, and a separate exercise and boxing space.

2–9 May

$391 SGD per night

Guest favourite

Guest house in Southbury

4.93 out of 5 average rating, 266 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).

18–25 Jul

$211 SGD per night

Guest favourite

Home in Danbury

4.99 out of 5 average rating, 336 reviews

BEAUTIFUL PRIVATE APARTMENT SUITE IN DANBURY CT!!

Private 1100 sq. Ft. suite staycation located in a beautiful, safe, quiet neighborhood in DanburyModern Kitchen, One Bathroom, One Luxury Queen Size Bed, 55” Smart TV with Cable/Amazon Prime/Netflix, Apple Cable charger next to bed, Wi-Fi, AC, Heat, Refrigerator, Countertop Oven, Microwave, Electric Hot Plate, Keurig Coffee Maker, Hair Dryer, Iron, Ironing Board, Shampoo, Conditioner, Body Wash. The space is nonsmoking inside and outside the premises including vaping. No children or infants

27 Dec – 3 Jan

$223 SGD per night

Guest favourite

Guest house in Newtown

4.79 out of 5 average rating, 19 reviews

Cozy Stay in Newtown - discounts for long term

1 Bed Room 1 Bath Apartment (shared wall) close to the quaint Sandy Hook Village, filled with restaurants, a wine bar, brewery, vineyard, boutiques, cafés, and beautiful scenery with walking trails. Easy access to exit 10 84. Plenty of natural light. Peaceful and quiet neighborhood perfect for a get away or work trip. This is a residential apartment - no shared entrances or access to space from main house, but it is a shared property. Stays longer than 31 days, inquire for discounted rate.

25 Sep – 2 Oct

$147 SGD per night

Superhost

Home in Roxbury

4.84 out of 5 average rating, 49 reviews

Laura in the Woods

The team at Elsa and Ramona--two of Brooklyn's warmest cocktail bars--have created a unique getaway for anyone needing a little time away from the city. This stunning light-filled house brings peace and restoration, surrounding you with nature in all seasons with maximal comfort and style. A great place to unwind for the weekend with friends, celebrate a milestone birthday, or even host a small wedding. Check out the amazing farm stands, hiking trails, & the famed Mayflower Spa down the street.

24–31 Oct

$701 SGD per night

Guest favourite

Guest suite in Watertown

4.91 out of 5 average rating, 162 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!

15–22 Jul

$98 SGD per night

Guest favourite

Loft in Woodbury

5.0 out of 5 average rating, 31 reviews

Country Loft

Sit back and relax in this recently renovated one bedroom apartment in the heart of historical Woodbury, CT. This loft-style apartment has an open floor plan, feeling spacious while still establishing moments of privacy. It is designed down to the tiniest details to be a comfortable, inviting space, perfect for anyone wanting to explore the Litchfield County area. Conveniently located on Antiques Row, the apartment is within walking distance of various attractions and the local organic market.

27 Jan – 3 Feb

$199 SGD per night

Guest favourite

Guest suite in Bethlehem

4.99 out of 5 average rating, 200 reviews

Breezy Crest private & restful w/antique charm

Escape to this charming and historic two-story 1841 suite, nestled in the quaint town of Bethlehem. The upstairs bedroom boasts original exposed beams and antique details, creating a cozy and inviting atmosphere. Wake up to the sunrise from the comfort of your bed and enjoy a warm fire in the backyard while listening to the peaceful sounds of nature. Conveniently located between Litchfield and Woodbury, and just 90 miles from NYC, you'll have easy access to shops, restaurants, and ski slopes.

30 Aug – 6 Sep

$225 SGD per night

Guest favourite

Flat in Brookfield

4.94 out of 5 average rating, 184 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.

23–30 Nov

$167 SGD per night

Guest favourite

Guest suite in Washington

5.0 out of 5 average rating, 36 reviews

Custom industrial farmhouse Apt in Washington Dpt

Cozy and quiet one bedroom suite with a full kitchen. This space is on the 2nd floor over an attached garage with an entrance separate from the main house. It is newly constructed and has its own heat and AC, complete kitchen, full bath with shower and queen sized bed. Just around the bend from Steep Rock Land Preserve and walking trails, and convenient to the center of town with galleries, restaurants and shops.

28 Aug – 4 Sep

$174 SGD per night

Guest favourite

Guest suite in Morris

4.99 out of 5 average rating, 340 reviews

Lakeside Private Guest Suite

Feel like you're in your own studio apartment in the spacious, bright lower level of our home! Walk out to your own private lounging/dining area. Separate entrance and parking space. Enjoy the serenity of Camp Columbia state park, as it is our extended backyard. Tip: The sunsets are beautiful! 2 hours from NYC, 30-45 minutes to local skiing and just 10 minutes to Washington Depot.

19–26 Nov

$127 SGD per night

Guest favourite

Flat in Bethlehem

4.94 out of 5 average rating, 225 reviews

Cozy 2nd Floor Suite In Bethlehem CT

Our private 2nd floor suite is fully equipped and easy on the budget. Sleeps 2 in comfort in queen bedroom, spacious living room and well equipped kitchenette. Dedicated workspace. Relax with Wi-Fi, Netflix, Amazon Prime, Sling TV , PBS, Pandora, etc. Free calls anywhere in the US.

1–8 May

$171 SGD per night