Vacation rentals in Ashford

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Top-rated vacation rentals in Ashford

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Guest favorite
The charming lake house features a sun-themed front entrance, flanked by dark shutters. A welcoming path leads to the door, surrounded by lush greenery and flower beds. The serene lake can be glimpsed through the trees in the background, enhancing the tranquil setting.
Home in Eastford
4.91 out of 5 average rating, 120 reviews

Serenity Ashford Lake

Serenity Ashford Lake is truly a gem far from the hustle and bustle of everyday life, while still enjoying all the creature comforts. Situated on the shores of tranquil Ashford lake, the Serenity lake house is definitely your place to relax and unwind. Waterfront jacuzzi, gazebo, central air, stainless steel appliances, cozy linens, washer/dryer, kayaks, firepit, boutique toiletries and a new kitchen space make up this beautiful lake home. Bring your favorite books, relax, and enjoy lake time!

Top guest favorite
A spacious studio apartment features a queen bed with a light-colored coverlet. A cozy seating area includes a sofa and a colorful patterned chair next to a small table. Bright light from a floor lamp highlights the room, while a ceiling fan adds comfort.
Apartment in Woodstock
4.97 out of 5 average rating, 29 reviews

Quiet Corner Studio

Kick back and relax in our calm,stylish space.This studio apt features a separate entrance in back of garage.A staircase leads up to a deck with a table and chairs for outdoor dining and relaxing.Catch a glimpse of our Highland cows peacefully grazing the day away.This studio apt is cozy,thoughtfully decorated, and stocked with all your necessities.Queen bed,Full size refrigerator, stove/oven, kuerig,toaster,microwave.Linens,blankets,pillows,throw pillows,towels.Your home away from home awaits!

Top guest favorite
The exterior of a bright red caboose is captured against a backdrop of tall trees. Sunlight filters through branches, highlighting the unique structure. A pathway of gravel leads to the entrance, which features steps and a small platform. The inviting colors complement the natural surroundings.
Guesthouse in Brooklyn
5 out of 5 average rating, 65 reviews

Historic Railroad Caboose - Unique CT Farm Escape

🚂 Authentic 1906 SOO-Line Caboose on our working CT horse farm! Queen Murphy bed + two bunks, WiFi, Roku, microwave, fridge, Keurig, deck, and cozy bathroom. Note: The historic 22" doorways limit accessibility. Explore nearby: Mashamoquet Brook trails, antique shops, wineries, and Putnam's arts district. Farm life starts early! Fall asleep to railroad dreams, wake to countryside serenity. Note: historic charm means cozy dimensions. Book today—before this experience leaves the station! 🌿

Top guest favorite
The exterior of a spacious barn structure is visible against a clear blue sky. The building features a gabled roof and light-colored wooden siding. Large double doors are positioned at the front, with a smaller door on the side. Leafless trees surround the barn.
Barn in Hampton
5 out of 5 average rating, 60 reviews

Little Rest Studio

Little Rest Studio overlooks 100 acres of conservation land, primarily oak and hickory forest. Recently renovated by the owners and full of personal, handmade touches, this apartment was originally conceived as a temporary ARTIST’S residence and occupies the top story of an English-style BARN otherwise used as a photographer's WORKSHOP. We offer a chance to slow down and meet the season, relax in the warmth of the wood stove or the bath, and be a human in a lovingly handmade retreat.

Guest favorite
The cabin is positioned near Lake Chaffee, featuring a deck area with seating for outdoor relaxation. Surrounding trees add a natural backdrop, while the sunset casts warm light over the landscape. The tranquil lake reflects the colors of the evening sky.
Cabin in Ashford
4.84 out of 5 average rating, 144 reviews

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

The Hidden Gem of Connecticut: Experience Lakefront bliss at our charming cabin boasting breathtaking water views of Lake Chaffee. ● 371 Mbps Wi-Fi | 50” 4K UHD Smart TV | Washer & Dryer | Indoor Fireplace ● 3x Kayaks | 2x Stand Up Paddle Boards | Private Dock | Outdoor Fireplace ● “Pink” Record Player w/ Vinyl Collection | Board Games ● Patio w/ Gas Grill | Full Kitchen | Coffee (Keurig) Drive to: ● UCONN (10 Mins) | Hartford (20 Mins) | Boston (1 Hour) | NYC (2 Hours)

Guest favorite
The exterior of a red, two-story building is surrounded by a well-maintained lawn featuring trees and landscaped flower beds. A large window above the entrance and additional windows enhance the farmhouse aesthetic. Cloudy skies and natural light create a serene atmosphere.
Farm stay in Woodstock
4.98 out of 5 average rating, 227 reviews

Barn suite at Southwood Alpacas

Country living at its best. Renovated guest space on a working alpaca farm. This is a two story unit with a kitchenette, living room and bathroom on the first floor and a studio loft on the second floor. Two decks, one on each level overlook the farm. Recently renovated. Great light floods the unit. Central heat & AC. Enjoy the farm and the bucolic setting in Woodstock. Watch the alpaca from your windows or deck. Cafes for morning breakfast and fine dining await.

Top guest favorite
A charming two-story house is framed by lush green trees and manicured lawns. The front porch offers an inviting entrance, while large windows allow for natural light. The surroundings are peaceful, enhancing the serene country setting.
Apartment in Ashford
4.96 out of 5 average rating, 213 reviews

On The Run Farm

Quiet country setting, minutes from UCONN and easy access from RTE 84 makes this place perfect for visitors traveling through the "Quiet Corner" of CT. Spacious living room, bedroom. kitchen and bath are newly renovated with, hardwood floors, skylights, and windows that allow for lots of natural light. The entryway is private with a lovely porch that is a great place to sit with your morning coffee. Hiking trails can be accessed from the property.

Superhost
A rustic cabin exterior is presented, featuring a stone chimney and wooden siding. Lush green grass surrounds the property, with a gravel driveway leading to the entrance. Trees provide shade, enhancing the tranquil outdoor setting.
Home in Ashford
4.84 out of 5 average rating, 128 reviews

Amazing lake home w/ amenities.

Escape to Lake Chaffee! This bright, airy lakefront home is peaceful and relaxing, with a private master, loft with twin bed, futon, and rollaway cot; perfect for couples or families. Paddle the lake, unwind by the fire pit, or cozy up indoors with Wi-Fi. Enjoy serene views year-round and unplug in comfort. Very quiet neighborhood on dead end street that lets you walk to one of the two beaches on the lake. You won’t be disappointed!

Guest favorite
The living room showcases a comfortable seating area with a dark couch, complemented by a glass dining table nearby. A wooden mantel above a decorative fireplace adds warmth, while natural light filters through the large windows, illuminating the soft white walls.
Apartment in Ashford
4.98 out of 5 average rating, 283 reviews

Enjoy a Farm Stay without the Work

This 3-room one-story apartment with private entrance is attached to the main 1850 farmhouse and also has that older farm charm. Only 10 minutes to Interstate 84 and midway between New York City and Boston, this location allows for ease of access to experiences in the northeast. The property is set back from the state road (Route 89) and allows for relaxed living on a beautiful farm bordered by stone walls and wooded area behind.

Top guest favorite
Guest suite in Mansfield
4.96 out of 5 average rating, 236 reviews

Cozy private apt 8 mins from UCONN - solar powered

Relax & unwind in this amply sized private studio suite, complete with large seating/tv area & study/desk space. Space comes w/ 2 beds (1 queen, 1 full sized pull out futon couch) a full private bath, mini-fridge, cooktop, microwave, dishware, & utensils. Beautiful rural wooded area with numerous hiking trails nearby. Longer term rentals may be considered starting from Summer of 2025

Top guest favorite
A spacious deck is presented, featuring wooden railings that overlook a serene landscape. Trees line the view, casting soft shadows on the deck's surface, with sunlight illuminating the area. The tranquil surroundings suggest an ideal setting for relaxation.
Guesthouse in Ashford
5 out of 5 average rating, 16 reviews

Chez Nanou- Above the Barn Charm

Take it easy at this unique and tranquil getaway. Chez Nanou is surrounded by conservation land, yet near shopping, restaurants, scenic roadways, and UCONN. Spend the day hiking on many trails nearby, go antiquing in Putnam, visit farms for apple picking in season, enjoy the charm of local distilleries, play a little piano on the Steinway, or just relax on the deck.

Top guest favorite
The entrance of the bungalow is shown, featuring a dark door with the number 106 clearly displayed. A wooden pathway leads up to the door, and greenery surrounds the area, including trees and shrubs, contributing to a natural and inviting setting.
Cabin in East Haddam
5 out of 5 average rating, 26 reviews

Bashan Lake Bungalow

Welcome to the Bashan Lake Bungalow! This charming, newly renovated cabin is designed for a relaxing, stress-free stay. Nestled in the heart of East Haddam, Connecticut, and surrounded by scenic state parks, the Bungalow offers beautiful views of Bashan Lake. Spend your time here unwinding, hiking the nearby trails, or simply enjoying the peaceful surroundings.

Popular amenities for Ashford vacation rentals