Holiday rentals in Connecticut

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Top-rated holiday rentals in Connecticut

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

Guest favourite
Treehouse in Thompson
The Tree House at Underhill Hollow
The Treehouse is a place where magic happens. Whether you’re looking for a romantic getaway, a family vacation or both. Sleep amongst the trees on a 7 acre 1825 farm. Meet Whirly, Gig and Belle. Find all 7, fairy houses. Go on a treasure hunt. Poke about our paths or explore the Airline trail, just off the property. S’mores, campfires, ghost stories and more. Meet our chickens. Spot deer, ducks or “Blue”, our resident blue heron. Adventure is in the air at the Hollow. Or nap in the hammock.
25 Mar – 1 Apr
£111 per night
4.96 out of 5 average rating, 327 reviews
Guest favourite
Flat in Milford
Water front studio apartment with fireplace.
This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!
28 Aug – 4 SeptIndividual Host,
£186 per night
4.97 out of 5 average rating, 505 reviews
Guest favourite
Cottage in Waterford
Classic CT Cottage w/ Trail by Harkness Park/Ocean
Tastefully appointed! A quaint cottage in a forest setting on 6 acres bordering Harkness State Park. A peaceful & serene setting where you can hear nature by day and the lighthouse sound signal at night. The cottage is fully equipped & very comfortable for your stay. The Waterford beach is a short drive away...less than 2 miles through the forest...as are beautiful hikes along the coast. Centrally located near Historic Mystic, Niantic, Conn College, US Coast Guard Academy & the US Naval Base.
13–20 AprIndividual Host,
£149 per night
4.99 out of 5 average rating, 102 reviews

Popular amenities for Connecticut holiday rentals

Other great holiday rentals in Connecticut

Guest favourite
Flat in Stamford
Sugar Shack Studio | Downtown Skyline Views
14–21 Feb
£136 per night
4.96 out of 5 average rating, 114 reviews
Guest favourite
Guest house in Glastonbury
Unique luxurious private building in historic area
21–28 AprIndividual Host,
£153 per night
4.96 out of 5 average rating, 133 reviews
Guest favourite
Home in Cheshire
Pool House
15–22 Jan
£133 per night
5.0 out of 5 average rating, 116 reviews
Guest favourite
Flat in West Haven
! ! ! entire apartment close to the beach ! !
10–17 DecIndividual Host,
£104 per night
4.9 out of 5 average rating, 411 reviews
Guest favourite
Guest house in Sharon
Cottage with a Waterfall View
3–10 MayProfessional Host,
£96 per night
5.0 out of 5 average rating, 58 reviews
Guest favourite
Home in Haddam
Cozy Comforts!
14–21 Sept
£118 per night
5.0 out of 5 average rating, 68 reviews
Guest favourite
Cabin in Milford
Long Stays! Charming Coast Cabin| Near Beach| Pets
12–19 AprIndividual Host,
£101 per night
5.0 out of 5 average rating, 12 reviews
Guest favourite
Flat in Milford
The Pond Mill Retreat w/ 2 Bdrms & Pool
30 Mar – 6 Apr
£133 per night
5.0 out of 5 average rating, 46 reviews
Guest favourite
Flat in Clinton
Cozy Shoreline Getaway
10–17 May
£102 per night
4.98 out of 5 average rating, 48 reviews
Guest favourite
Guest suite in Wilton
Guest suite with private enter
16–23 Apr
£84 per night
5.0 out of 5 average rating, 20 reviews
Guest favourite
Tiny home in West Greenwich
Waterfront lake home 1 Bed 1 Bath cottage
26 Jan – 2 Feb
£106 per night
4.89 out of 5 average rating, 37 reviews
Guest favourite
Home in East Haddam
Romantic Getaway at The Lake!
23–30 Aug
£207 per night
4.95 out of 5 average rating, 84 reviews

Destinations to explore