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Cottages, Villas, Apartments in Portland
Holiday Rentals
USA
Connecticut (CT)
Cottages, Villas, Apartments in Portland
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Internet or Wifi (41)
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Kid friendly (34)
Pet friendly (11)
Smoking allowed (1)
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Holiday Rental House (31)
Condominium/Apartment (11)
Cabin Holiday Rental (0)
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Waterfront (12)
Boat Available (4)
Private Chef (0)
Private Beach (0)
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Distance from
5 mi
Brownstone Exploration & Discovery Park
Gotta's Farm and Cider Mill
Arrigoni Winery
Quarry View Historic Park
Concentric Brewing Company
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42 rentals
in Portland.
The following properties within 20 miles of Portland match all your filters:
Tiny Lakefront Cottage!
34
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Peaceful lake cottage #2
24
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Cozy newly remodeled home close to major amenities in Connecticut a
13
Holiday Rental House
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4 bedrooms
1 bathroom
Sleeps 6
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Sleeps
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As seen on
Lake Front Cottage #7!
16
Condo/Apartment
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0 bedrooms
1 bathroom
Sleeps 2
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Sleeps
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Romantic Lakefront Cottage #5
20
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 2
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Sleeps
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Amazing Lakefront Property
12
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 10
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Sleeps
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As seen on
Lake Front Home.....
25
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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Sleeps
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Fun Lake Front Cottage!
22
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Sleeps
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As seen on
Cozy Lakefront Cottage #6
9
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
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Sleeps
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lakefront estate
8
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 10
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Sleeps
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Historic Mansion 1841
5
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 7
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Sleeps
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As seen on
Cozy Getaway w/lots of Natural Light :) 5 mins to adventures
5
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 2
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Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
13
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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As seen on
Family Friendly,Lakefront Cottage, 1 dock, private, easy access from I 91.
10
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Sleeps
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As seen on
The Braswell
1
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 6
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Little House on River - architectural gem
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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As seen on
Cabin Deck House - Formidable Cabin in Laurel Island
Holiday Rental House
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4 bedrooms
1 bathroom
Sleeps 10
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As seen on
Modern Middletown Retreat, Minutes to Downtown!
Condo/Apartment
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4 bedrooms
1 bathroom
Sleeps 6
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As seen on
Lovely Family sized 3 bedroom Colonial home, close to restaurant.
10
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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As seen on
Direct Lakefront, 2 docks, private, easy access from I 91.
7
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
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Sleeps
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As seen on
Luxury Waterfront Lake House by Ski Resort & Winery
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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As seen on
Elegant Middlefield Getaway w/ Game Room!
4
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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As seen on
Charming private home on the Connecticut River that comfortably sleeps 11 people
6
Holiday Rental House
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5 bedrooms
2 bathrooms
Sleeps 12
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As seen on
Magnificent river front home located directly on the CT River
112
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 9
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As seen on
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
5
Holiday Rental House
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3 bedrooms
4 bathrooms
Sleeps 6
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As seen on
The Little Nest-Cozy & Adorable cottage just a short walk to Lake Pocotopaug!
4
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
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Sleeps
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As seen on
John Hollister home on the farm
2
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 12
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Sleeps
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As seen on
Modern Luxury, The Perfect Getaway Awaits
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 7
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Sleeps
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As seen on
Luxe Lake House in Connecticut
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 11
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Sleeps
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As seen on
NEW! Charming Riverside Home-CT River Private, Spacious, Family & Pet Friendly
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
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As seen on
Conference Room Rental no sleeping arrangements
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 30
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As seen on
Downtown Dream| Meriden Metro| Cozy Retreat Studio
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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As seen on
Middletown Guest Suite Near Dtwn & University
Condo/Apartment
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3 bedrooms
3 bathrooms
Sleeps 5
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As seen on
Charming Castle Cottage
4
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Sleeps
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As seen on
Alongside ski area. Charming house in Middlefield, 2 hrs from NY or Boston
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 4
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Sleeps
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As seen on
Charming Connecticut Hideaway
1
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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Sleeps
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As seen on
Private Apt in Middletown-Wesleyan
2
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 5
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Sleeps
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Family Stays: Middletown, CT
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
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Sleeps
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As seen on
Modern 3 Bedroom Lake House- Close To Restaurants and Beach Access
4
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Sleeps
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As seen on
Luxury Estate, Elegant, Private-2 miles from Wesleyan University-The White Lion
9
Holiday Rental House
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9 bedrooms
10 bathrooms
Sleeps 16
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As seen on
Newly renovated! 3 bedroom apt in downtown Middletown - across from Wesleyan
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 7
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As seen on
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
6
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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1
Showing results 1-42 of 42
Frequently Asked Questions about Portland
Do any holiday rentals in Portland have a pool?
Yes, here are some popular holiday rentals in Portland that have a pool:
Tiny Lakefront Cottage!
Peaceful lake cottage #2
Cozy newly remodeled home close to major amenities in Connecticut a
See all holiday rentals with a pool in Portland on Tripadvisor
Do any holiday rentals in Portland have internet access?
Yes, here are some popular holiday rentals in Portland that have internet access:
Tiny Lakefront Cottage!
Peaceful lake cottage #2
Cozy newly remodeled home close to major amenities in Connecticut a
See all holiday rentals in Portland on Tripadvisor
What are the best pet friendly rentals in Portland?
The best pet friendly rentals in Portland are:
Cozy newly remodeled home close to major amenities in Connecticut a
The Braswell
Cabin Deck House - Formidable Cabin in Laurel Island
See all pet friendly holiday rentals in Portland on Tripadvisor
What are some great rentals in Portland that are kid friendly?
Some of the most popular kid friendly rentals in Portland are:
Peaceful lake cottage #2
Cozy newly remodeled home close to major amenities in Connecticut a
Amazing Lakefront Property
See all kid friendly holiday rentals in Portland on Tripadvisor
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