Holiday rentals in Stonington

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Top-rated holiday rentals in Stonington

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

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Top guest favourite
A serene landscape is presented, featuring expansive green fields under a softly glowing sunrise. Two rustic buildings are visible: a barn with classic doors and a white cottage, both surrounded by lush trees and open space, reflecting the peaceful countryside setting.
Guest house in North Stonington
4.99 out of 5 average rating, 223 reviews

"Mystic Country" Farm Stay at 100 Acre Wood

Let us welcome you to 100 Acre Wood, a historic farm and working cattle ranch. Owl's House is a private and stylish guest house nestled within the trees and garden and offers 180° views. Our farm store is stocked with our own TX Longhorn beef and pasture-raised chicken and eggs, plus curated with local products. Enjoy pastoral farm life and our private forest trails, or get out and play in the area's abundance of fine dining, wineries, seasonal attractions, outdoor activities, and entertainment.

Guest favourite
A spacious living area features a comfortable sectional sofa facing a sleek coffee table. Natural light floods in through large windows, highlighting the polished wood floor. A modern kitchen with bar stools is visible in the background, creating an inviting open layout.
Flat in Stonington
4.93 out of 5 average rating, 123 reviews

Stevedore Landing-#3 · walk Mystic-Train/EV Lvl-2

Perfect for a couples' getaway. Experience the charm and beauty of Mystic at Mystic Harbor Landing. This stunning 1 bedroom boasts breathtaking water views of the Mystic Harbor. Take a short 10 minute walk to the Mystic Amtrak or 15 minute to the historic downtown area. Fully renovated with all new appliances, bathroom and kitchen, you will feel like home . Whether you're planning a small family vacation or a romantic getaway, The Mystic Harbor Landing is the perfect escape. Level-2 EV charging

Top guest favourite
A charming red colonial home stands proudly beside a tree-lined street. The white picket fence surrounds the front yard, which is adorned with greenery and patriotic bunting. Large trees provide shade, creating a welcoming atmosphere for visitors.
Home in Old Mystic
5 out of 5 average rating, 144 reviews

Nautical "Hallmark" Retreat~ 5 Toasty Fireplaces!

Play the lead in your very own seafaring fable when you stay at the 1784 Denison Home. Our lovingly restored, dog-friendly New England vacation home is located in the hamlet of Old Mystic near the head of the Mystic River~ around the corner from scenic River Rd. With 5 bedrooms/5 bathrooms, it accommodates 10 guests very comfortably. Think Colonial charm combined with modern amenities for 21st-century comfort and a splash of pure, homegrown hospitality to make your Mystic stay most relaxing!

Guest favourite
A glass desk is positioned beside large windows, offering views of the water and sky. A cozy chair with a fluffy seat cover complements the desk. A stack of books, binoculars, and a soft-lit lamp are arranged on the desk, enhancing the workspace atmosphere.
Flat in Stonington
4.94 out of 5 average rating, 316 reviews

Mystical Ocean View in Historic Stonington Borough

Enjoy stunning ocean views of Stonington Harbor and Fishers Island Sound from multiple floors of this spacious, comfortable apartment for 6. Located in historic Stonington Borough, Connecticut's oldest village, you can relax in the private library, then explore this picturesque area with acclaimed restaurants, shops, and museums all within walking distance. And with Downtown Mystic, I-95, and RI's beaches just a short drive away, you can have it all, located half way between Boston and NYC!

Top guest favourite
A cozy cottage exterior is showcased, featuring a gabled roof and wooden siding in earthy tones. A spacious screened porch with rocking chairs invites relaxation, while a nearby shed complements the rustic aesthetic. Surrounding nature highlights seasonal foliage, enhancing the tranquil setting.
Home in Stonington
4.96 out of 5 average rating, 200 reviews

Romantic Seaside Cottage in Mystic

This cozy seaside cottage with sleep loft has the look and feel of an old classic yacht inside with modern amenities. Couples will love the water views, screened porch, gas-wood stove, heated stone floor in cedar bathroom, outdoor shower and patio. Another larger 2 bedroom cottage on property is for rent also for families with younger children. This rental is NOT suitable for toddlers or children under 12 due to the open balconies, railings and narrow spiral staircase to the loft.

Top guest favourite
Guest suite in Stonington
4.99 out of 5 average rating, 325 reviews

Morgan Suite - spacious | hot tub | water views!

The Morgan Suite is a private Airbnb located in a quiet neighborhood along the Pawcatuck River. Just minutes to downtown Westerly, downtown Mystic, beaches, breweries, wineries, shops, restaurants and much more. This Airbnb a perfect for a romantic getaway or a relaxing memorable vacation with a friend. If you are looking to explore a new area and relax, the Morgan Suite is for you! The home is spacious, newly renovated with excellent amenities. Newly added - hot tub and massage chair!

Guest favourite
A dining area features a wooden table surrounded by six upholstered chairs. Natural light fills the space through large windows adorned with sheer curtains. A shelf in the background displays various decorative items, enhancing the room's inviting atmosphere.
Townhouse in Stonington
4.86 out of 5 average rating, 258 reviews

Lovely Victorian Townhouse in Downtown Mystic

Walkable to everywhere! This lovely 2 bed / 2 bath Victorian townhouse has been remodeled to a luxury standard. The highlights of the property are two fabulous bathrooms, one featuring a gorgeous copper soaker tub, and the other featuring sumptuous marble tiling and a walk-in Delta rain shower. It also features a gourmet farm-style kitchen, and has its own separate and direct entrance that is not share with anyone. Well-behaved pets are welcome for an additional fee of $60.

Top guest favourite
A serene bedroom features a spacious bed adorned with soft grey linens. Two bedside tables, each with a lamp, flank the bed. A vibrant piece of artwork and a framed print add color to the walls, enhancing the room’s inviting ambiance.
Guest suite in Westerly
4.98 out of 5 average rating, 163 reviews

Private suite close to beaches and downtown.

The Ruedemann Suite is situated off of our main house in a quiet neighborhood. We are located 3 miles from Misquamicut Beach & Watch Hill. Historic Downtown Westerly with its thriving restaurant, arts & music scene is 1.5 miles from the house. Take a short drive to Stonington or Mystic for shopping or local vineyards. Feeling lucky? Mohegan Sun & Foxwoods Casinos are close by! Newport & Providence are a 45-minute drive. Follow on the gram @ruedemannsuite

Top guest favourite
Home in Stonington
4.98 out of 5 average rating, 121 reviews

FREE Private Indoor Heated Pool - Mystic Home

Experience Mystic in style at this spacious retreat with a private year-round heated indoor pool. Sleeps up to 11 with 4 king beds + bunk, 3 full baths, and open living spaces perfect for groups. Relax poolside, cook in the gourmet kitchen, or gather on the patio by evening. Walk to downtown Mystic’s shops, restaurants, and attractions. Designed for comfort and convenience, this home is your perfect coastal escape!

Top guest favourite
A spiral staircase with a sleek black railing leads to the loft bedroom. A mirror with a burgundy frame is mounted against the wall, reflecting the light. The open living area features a light-colored couch and a wooden dining table, visible through large windows offering views of the outdoors.
Guest house in Mystic
4.98 out of 5 average rating, 669 reviews

Gorgeous Waterfront Getaway

Perfect getaway from the city for couples wanting peace and tranquility and stunning views. A beautiful waterfront one bedroom guesthouse, one and one-half miles from downtown Mystic CT. Beautifully decorated with art and antiques. Kitchenette, full bath and loft bedroom. Queen bed. Air conditioning and heated. Belgian linen bedding! Private patio. Dock. Kayak/Canoe rentals close by. Internet.

Top guest favourite
A bright living area showcases a comfortable leather sofa paired with a colorful accent chair. Large windows allow natural light to fill the space, while a small globe and decorative items add a touch of character. Wooden floors complement the cozy atmosphere.
Cottage in Groton
4.96 out of 5 average rating, 339 reviews

Historic Waterfront School House

Escape to a historic 1857 schoolhouse cottage on the Mystic River. This unique 1-bed, 1-bath waterfront retreat is perfect for couples or solo travelers. Enjoy stunning views of the Mystic Drawbridge and Seaport from your private patio. Just a 2-block walk to historic Downtown Mystic, this charming space combines authentic history with modern comfort for an unforgettable stay.

Top guest favourite
A charming cabin with a red exterior sits surrounded by colorful autumn foliage, reflecting on the calm surface of a pond. A spacious deck is visible, featuring a patio chair and table, while a kayak rests nearby on the grassy shore.
Cabin in North Stonington
4.96 out of 5 average rating, 242 reviews

Come to the woods and snuggle in front of the fire

Come to the woods of Southeastern Connecticut and enjoy some solitude and connection in the woods while wrapped in our flannel LL Bean bathrobes. Snuggle with a glass of wine or coffee by the fire and unplug, rest, and rejuvenate with your partner or by yourself. Only fifteen minutes away from casinos, shopping or restaurants in Mystic or downtown Westerly, RI.

Popular amenities for Stonington holiday rentals

When is the best time to visit Stonington?

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Avg. price$261 SGD$253 SGD$267 SGD$282 SGD$320 SGD$351 SGD$385 SGD$386 SGD$336 SGD$316 SGD$289 SGD$289 SGD
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Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Stonington?

    Yes! Work meets play with ease at over 310 vacation rentals in Stonington featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Stonington?

    Four-legged friends are welcome in Stonington. Choose from more than 180 vacation rentals for guests traveling with pets.

  • Are there Stonington vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Stonington, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in bed and breakfast rentals in Stonington?

    Experience the best of Stonington with our bed and breakfast rentals, starting at about $230 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in Stonington have a bbq area?

    Absolutely! We offer over 20 apartment rentals with a bbq area in Stonington. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Stonington have wifi?

    Absolutely! We offer over 150 apartment rentals with wifi in Stonington. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Stonington have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Stonington. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Stonington have self check-in?

    Absolutely! We offer over 100 house rentals with self check-in in Stonington. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly apartment rentals in Stonington?

    Stonington has more than 80 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Apartment Rentals in Stonington?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 50 homes with self check-in, over 20 homes with a bbq area, over 150 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Stonington

  • Total holiday rentals

    Explore 560 holiday rentals in Stonington

  • Nightly prices starting at

    Stonington holiday rentals start at $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 36,190 verified reviews to help you choose

  • Family-friendly holiday rentals

    380 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 180 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    310 properties have a dedicated workspace

  • Wifi availability

    550 of Stonington holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Stonington rentals

  • 4.9 Average rating

    Stonington stays are highly rated by guests – averaging 4.9 out of 5!

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