Vacation Rentals in Connecticut
Explore 2,742 vacation rental properties across 276 destinations in Connecticut.
276 destinations
2,742 verified listings
Updated March 2026
All destinations in Connecticut
276 cities New Haven
158 properties Explore →
Stonington
135 properties Explore →
Milford
100 properties Explore →
Mystic
93 properties Explore →
Stamford
84 properties Explore →
Old Saybrook
82 properties Explore →
Westbrook
74 properties Explore →
Old Lyme
71 properties Explore →
Fairfield
57 properties Explore →
Madison
56 properties Explore →
Westport
55 properties Explore →
Branford
53 properties Explore →
Norwich
52 properties Explore →
Greenwich
52 properties Explore →
Groton
51 properties Explore →
Bridgeport
47 properties Explore →
East Lyme
43 properties Explore →
Clinton
42 properties Explore →
Hartford
40 properties Explore →
Guilford
38 properties Explore →
New Fairfield
37 properties Explore →
Waterford
36 properties Explore →
New Milford
35 properties Explore →
Norwalk
35 properties Explore →
New London
33 properties Explore →
East Haven
29 properties Explore →
Danbury
27 properties Explore →
Westerly
26 properties Explore →
Litchfield
24 properties Explore →
Washington
24 properties Explore →
West Haven
22 properties Explore →
Montville
21 properties Explore →
Wallingford
19 properties Explore →
East Hampton
18 properties Explore →
West Hartford
18 properties Explore →
Morris
18 properties Explore →
Coventry
17 properties Explore →
Southington
17 properties Explore →
Roxbury
17 properties Explore →
Weston
16 properties Explore →
Niantic
15 properties Explore →
Brookfield
15 properties Explore →
White Plains
15 properties Explore →
Waterbury
14 properties Explore →
Bristol
14 properties Explore →
Warren
14 properties Explore →
Manchester
14 properties Explore →
Salisbury
13 properties Explore →
Hamden
13 properties Explore →
Stratford
13 properties Explore →
Sharon
12 properties Explore →
Avon
12 properties Explore →
East Haddam
12 properties Explore →
Middletown
11 properties Explore →
New Britain
11 properties Explore →
Goshen
11 properties Explore →
Middlefield
10 properties Explore →
Glen Cove
10 properties Explore →
Millerton
10 properties Explore →
Torrington
10 properties Explore →
Bloomfield
9 properties Explore →
Newtown
9 properties Explore →
Wading River
9 properties Explore →
South Salem
9 properties Explore →
Charlestown
9 properties Explore →
Glastonbury
9 properties Explore →
Mount Vernon
9 properties Explore →
winsted
8 properties Explore →
New Preston
8 properties Explore →
Kent
8 properties Explore →
Meriden
8 properties Explore →
East Marion
8 properties Explore →
Sheffield
8 properties Explore →
Windsor
7 properties Explore →
Ashford
7 properties Explore →
Bethlehem
7 properties Explore →
Woodbury
7 properties Explore →
Lebanon
7 properties Explore →
Colchester
7 properties Explore →
Sherman
7 properties Explore →
Dover Plains
7 properties Explore →
Tolland
7 properties Explore →
Essex
6 properties Explore →
Watertown
6 properties Explore →
Rocky Hill
6 properties Explore →
Granby
6 properties Explore →
Old Mystic
6 properties Explore →
Pound Ridge
6 properties Explore →
Killingworth
6 properties Explore →
Holland
6 properties Explore →
New Rochelle
6 properties Explore →
Plainville
6 properties Explore →
Farmington
6 properties Explore →
New Marlborough
6 properties Explore →
Suffield
6 properties Explore →
Harwinton
5 properties Explore →
North Stonington
5 properties Explore →
Redding
5 properties Explore →
Plymouth
5 properties Explore →
New Hartford
5 properties Explore →
Downtown New Haven
5 properties Explore →
Ansonia
5 properties Explore →
Darien
5 properties Explore →
Trumbull
5 properties Explore →
Easton
5 properties Explore →
Lyme
5 properties Explore →
Mamaroneck
5 properties Explore →
Norfolk
5 properties Explore →
Huntington Station
5 properties Explore →
Ridgefield
5 properties Explore →
Sandisfield
5 properties Explore →
Enfield
4 properties Explore →
Thompson
4 properties Explore →
Wolcott
4 properties Explore →
East Hartford
4 properties Explore →
Killingly
4 properties Explore →
North Haven
4 properties Explore →
Chester
4 properties Explore →
Deep River
4 properties Explore →
Ridge
4 properties Explore →
Rocky Point
4 properties Explore →
Calverton
4 properties Explore →
West Cornwall
4 properties Explore →
Canaan
4 properties Explore →
Simsbury
4 properties Explore →
Canton
4 properties Explore →
Ledyard
3 properties Explore →
Woodbridge
3 properties Explore →
Winchester
3 properties Explore →
Preston
3 properties Explore →
Woodstock
3 properties Explore →
Pawcatuck
3 properties Explore →
New Canaan
3 properties Explore →
Rowayton
3 properties Explore →
Baiting Hollow
3 properties Explore →
Webster
3 properties Explore →
Brimfield
3 properties Explore →
Pomfret
3 properties Explore →
Bantam
3 properties Explore →
Cornwall
3 properties Explore →
Amenia
3 properties Explore →
Lakeville
3 properties Explore →
Bridgewater
3 properties Explore →
Southwick
3 properties Explore →
Hebron
3 properties Explore →
Southbury
3 properties Explore →
Noank
3 properties Explore →
Sprague
2 properties Explore →
Voluntown
2 properties Explore →
Griswold
2 properties Explore →
Haddam
2 properties Explore →
Washington Depot
2 properties Explore →
Stonington (Old Mystic)
2 properties Explore →
Centereach
2 properties Explore →
Miller Place
2 properties Explore →
Mansfield
2 properties Explore →
Port Chester
2 properties Explore →
Huntington
2 properties Explore →
Hastings-on-Hudson
2 properties Explore →
Cheshire
2 properties Explore →
Falls Village
2 properties Explore →
Cornwall Bridge
2 properties Explore →
Oyster Bay
2 properties Explore →
Port Washington
2 properties Explore →
Larchmont
2 properties Explore →
The Bronx
2 properties Explore →
North Branford
2 properties Explore →
Wilton
2 properties Explore →
Thomaston
2 properties Explore →
Pine Plains
2 properties Explore →
Collinsville
2 properties Explore →
Colebrook
2 properties Explore →
Shelton
2 properties Explore →
Douglas
2 properties Explore →
Sturbridge
2 properties Explore →
greenport
2 properties Explore →
Bolton
2 properties Explore →
Pawling
2 properties Explore →
Brewster
2 properties Explore →
Bozrah
2 properties Explore →
Naugatuck
2 properties Explore →
Oxford
2 properties Explore →
Columbia
2 properties Explore →
Windham
2 properties Explore →
North Granby
1 property Explore →
oakdale
1 property Explore →
Old Mystic/Stonington
1 property Explore →
Old Mystic CT
1 property Explore →
Pawcutuck
1 property Explore →
Farifield
1 property Explore →
Southport
1 property Explore →
Greenwich, Cos cob
1 property Explore →
Orange
1 property Explore →
Shoreham
1 property Explore →
Sound Beach
1 property Explore →
Mt Sinai
1 property Explore →
East Setauket
1 property Explore →
West Redding
1 property Explore →
Middle Island
1 property Explore →
Derby
1 property Explore →
Mount Sinai
1 property Explore →
Ashaway
1 property Explore →
Groton Long Point
1 property Explore →
Higganum
1 property Explore →
East Haven, Connecticut
1 property Explore →
Guilford Center
1 property Explore →
Sutton
1 property Explore →
Dobbs Ferry
1 property Explore →
East Canaan
1 property Explore →
Middle Haddam
1 property Explore →
Northport
1 property Explore →
Watch Hill
1 property Explore →
Longmeadow
1 property Explore →
Old Wethersfield
1 property Explore →
East Windsor
1 property Explore →
East Granby
1 property Explore →
Newington
1 property Explore →
Ashley Falls
1 property Explore →
North Canaan
1 property Explore →
Bantam Litchfield
1 property Explore →
Cos Cob
1 property Explore →
Tarrytown
1 property Explore →
Harrison
1 property Explore →
Bayville
1 property Explore →
Rye Brook
1 property Explore →
Briarcliff Manor
1 property Explore →
Berlin
1 property Explore →
Cromwell
1 property Explore →
Weatogue
1 property Explore →
Glen Head
1 property Explore →
Scarsdale
1 property Explore →
Gaylordsville
1 property Explore →
Tuckahoe
1 property Explore →
Wingdale
1 property Explore →
Northford
1 property Explore →
Ancramdale
1 property Explore →
Barkhamsted
1 property Explore →
Shekomeko
1 property Explore →
Waccabuc
1 property Explore →
West Hartland
1 property Explore →
West Suffield
1 property Explore →
Russell
1 property Explore →
Charlton
1 property Explore →
Willington
1 property Explore →
Dudley
1 property Explore →
Wales
1 property Explore →
Canterbury
1 property Explore →
Burrillville
1 property Explore →
Portland
1 property Explore →
Sterling
1 property Explore →
Cold Spring Harbor
1 property Explore →
Syosset
1 property Explore →
Durham
1 property Explore →
Orient
1 property Explore →
Ellington
1 property Explore →
Vernon
1 property Explore →
Bethel
1 property Explore →
Salem
1 property Explore →
Uncasville
1 property Explore →
Prospect
1 property Explore →
Bethany
1 property Explore →
Middlebury
1 property Explore →
Andover
1 property Explore →
Marlborough
1 property Explore →
Ocean Beach Park
1 property Explore →
Terryville
1 property Explore →
Westfield
1 property Explore →
Blandford
1 property Explore →
North Grosvenordale
1 property Explore →
Stafford
1 property Explore →
Dayville
1 property Explore →
Abington
1 property Explore →
Halesite
1 property Explore →
Melville
1 property Explore →
Wallingfrd
1 property Explore →
Agawam
1 property Explore →