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Portland Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
42 rentals in Portland.
The following properties within 20 miles of Portland match all your filters:
Tiny Lakefront Cottage!, holiday rental in Portland
Tiny Lakefront Cottage!, holiday rental in Portland
Tiny Lakefront Cottage!, holiday rental in Portland

Tiny Lakefront Cottage!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Peaceful lake cottage #2, holiday rental in Portland
Peaceful lake cottage #2, holiday rental in Portland
Peaceful lake cottage #2, holiday rental in Portland

Peaceful lake cottage #2

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy newly remodeled home close to major amenities  in Connecticut a, holiday rental in Portland
Cozy newly remodeled home close to major amenities  in Connecticut a, holiday rental in Portland
Cozy newly remodeled home close to major amenities  in Connecticut a, holiday rental in Portland

Cozy newly remodeled home close to major amenities in Connecticut a

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lake Front Cottage #7!, holiday rental in Portland
Lake Front Cottage #7!, holiday rental in Portland
Lake Front Cottage #7!, holiday rental in Portland

Lake Front Cottage #7!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Romantic Lakefront Cottage #5, holiday rental in Portland
Romantic Lakefront Cottage #5, holiday rental in Portland
Romantic Lakefront Cottage #5, holiday rental in Portland

Romantic Lakefront Cottage #5

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Amazing Lakefront Property, holiday rental in Portland
Amazing Lakefront Property, holiday rental in Portland
Amazing Lakefront Property, holiday rental in Portland

Amazing Lakefront Property

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Lake Front Home....., holiday rental in Portland
Lake Front Home....., holiday rental in Portland
Lake Front Home....., holiday rental in Portland

Lake Front Home.....

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Fun Lake Front Cottage!, holiday rental in Portland
Fun Lake Front Cottage!, holiday rental in Portland
Fun Lake Front Cottage!, holiday rental in Portland

Fun Lake Front Cottage!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Lakefront Cottage #6, holiday rental in Portland
Cozy Lakefront Cottage #6, holiday rental in Portland
Cozy Lakefront Cottage #6, holiday rental in Portland

Cozy Lakefront Cottage #6

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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lakefront estate, holiday rental in Portland
lakefront estate, holiday rental in Portland
lakefront estate, holiday rental in Portland

lakefront estate

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Historic Mansion 1841, holiday rental in Portland
Historic Mansion 1841, holiday rental in Portland
Historic Mansion 1841, holiday rental in Portland

Historic Mansion 1841

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 7
Match: Sleeps
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Cozy Getaway w/lots of Natural Light :) 5 mins to adventures, holiday rental in Portland
Cozy Getaway w/lots of Natural Light :) 5 mins to adventures, holiday rental in Portland
Cozy Getaway w/lots of Natural Light :) 5 mins to adventures, holiday rental in Portland

Cozy Getaway w/lots of Natural Light :) 5 mins to adventures

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown, holiday rental in Portland
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown, holiday rental in Portland
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown, holiday rental in Portland

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Family Friendly,Lakefront Cottage, 1 dock, private, easy access from I 91., holiday rental in Portland
Family Friendly,Lakefront Cottage, 1 dock, private, easy access from I 91., holiday rental in Portland
Family Friendly,Lakefront Cottage, 1 dock, private, easy access from I 91., holiday rental in Portland

Family Friendly,Lakefront Cottage, 1 dock, private, easy access from I 91.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Braswell, holiday rental in Portland
The Braswell, holiday rental in Portland
The Braswell, holiday rental in Portland

The Braswell

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Little House on River - architectural gem, holiday rental in Portland
Little House on River - architectural gem, holiday rental in Portland
Little House on River - architectural gem, holiday rental in Portland

Little House on River - architectural gem

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cabin Deck House - Formidable Cabin in Laurel Island, holiday rental in Portland
Cabin Deck House - Formidable Cabin in Laurel Island, holiday rental in Portland
Cabin Deck House - Formidable Cabin in Laurel Island, holiday rental in Portland

Cabin Deck House - Formidable Cabin in Laurel Island

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Modern Middletown Retreat, Minutes to Downtown!, holiday rental in Portland
Modern Middletown Retreat, Minutes to Downtown!, holiday rental in Portland
Modern Middletown Retreat, Minutes to Downtown!, holiday rental in Portland

Modern Middletown Retreat, Minutes to Downtown!

Condo/Apartment
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lovely Family sized 3 bedroom Colonial home, close to restaurant., holiday rental in Portland
Lovely Family sized 3 bedroom Colonial home, close to restaurant., holiday rental in Portland
Lovely Family sized 3 bedroom Colonial home, close to restaurant., holiday rental in Portland

Lovely Family sized 3 bedroom Colonial home, close to restaurant.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Direct Lakefront, 2 docks, private, easy access from I 91., holiday rental in Portland
Direct Lakefront, 2 docks, private, easy access from I 91., holiday rental in Portland
Direct Lakefront, 2 docks, private, easy access from I 91., holiday rental in Portland

Direct Lakefront, 2 docks, private, easy access from I 91.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Waterfront Lake House by Ski Resort & Winery, holiday rental in Portland
Luxury Waterfront Lake House by Ski Resort & Winery, holiday rental in Portland
Luxury Waterfront Lake House by Ski Resort & Winery, holiday rental in Portland

Luxury Waterfront Lake House by Ski Resort & Winery

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Elegant Middlefield Getaway w/ Game Room!, holiday rental in Portland
Elegant Middlefield Getaway w/ Game Room!, holiday rental in Portland
Elegant Middlefield Getaway w/ Game Room!, holiday rental in Portland

Elegant Middlefield Getaway w/ Game Room!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Charming private home on the Connecticut River that comfortably sleeps 11 people, holiday rental in Portland
Charming private home on the Connecticut River that comfortably sleeps 11 people, holiday rental in Portland
Charming private home on the Connecticut River that comfortably sleeps 11 people, holiday rental in Portland

Charming private home on the Connecticut River that comfortably sleeps 11 people

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Magnificent river front home located directly on the CT River, holiday rental in Portland
Magnificent river front home located directly on the CT River, holiday rental in Portland
Magnificent river front home located directly on the CT River, holiday rental in Portland

Magnificent river front home located directly on the CT River

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
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Home away from home Hot Tub and Pool in Middletown home of Wesleyan university, holiday rental in Portland
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university, holiday rental in Portland
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university, holiday rental in Portland

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Little Nest-Cozy & Adorable cottage just a short walk to Lake Pocotopaug!, holiday rental in Portland
The Little Nest-Cozy & Adorable cottage just a short walk to Lake Pocotopaug!, holiday rental in Portland
The Little Nest-Cozy & Adorable cottage just a short walk to Lake Pocotopaug!, holiday rental in Portland

The Little Nest-Cozy & Adorable cottage just a short walk to Lake Pocotopaug!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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John Hollister home on the farm, holiday rental in Portland
John Hollister home on the farm, holiday rental in Portland
John Hollister home on the farm, holiday rental in Portland

John Hollister home on the farm

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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Modern Luxury, The Perfect Getaway Awaits, holiday rental in Portland
Modern Luxury, The Perfect Getaway Awaits, holiday rental in Portland
Modern Luxury, The Perfect Getaway Awaits, holiday rental in Portland

Modern Luxury, The Perfect Getaway Awaits

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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Luxe Lake House in Connecticut, holiday rental in Portland
Luxe Lake House in Connecticut, holiday rental in Portland
Luxe Lake House in Connecticut, holiday rental in Portland

Luxe Lake House in Connecticut

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
More info
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NEW! Charming Riverside
Home-CT River
Private, Spacious, Family & Pet Friendly, holiday rental in Portland
NEW! Charming Riverside
Home-CT River
Private, Spacious, Family & Pet Friendly, holiday rental in Portland
NEW! Charming Riverside
Home-CT River
Private, Spacious, Family & Pet Friendly, holiday rental in Portland

NEW! Charming Riverside Home-CT River Private, Spacious, Family & Pet Friendly

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Conference Room Rental no sleeping arrangements, holiday rental in Portland
Conference Room Rental no sleeping arrangements, holiday rental in Portland
Conference Room Rental no sleeping arrangements, holiday rental in Portland

Conference Room Rental no sleeping arrangements

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 30
Match: Sleeps
More info
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Downtown Dream| Meriden Metro| Cozy Retreat Studio, holiday rental in Portland
Downtown Dream| Meriden Metro| Cozy Retreat Studio, holiday rental in Portland
Downtown Dream| Meriden Metro| Cozy Retreat Studio, holiday rental in Portland

Downtown Dream| Meriden Metro| Cozy Retreat Studio

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Middletown Guest Suite Near Dtwn & University, holiday rental in Portland
Middletown Guest Suite Near Dtwn & University, holiday rental in Portland
Middletown Guest Suite Near Dtwn & University, holiday rental in Portland

Middletown Guest Suite Near Dtwn & University

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
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Charming Castle Cottage, holiday rental in Portland
Charming Castle Cottage, holiday rental in Portland
Charming Castle Cottage, holiday rental in Portland

Charming Castle Cottage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Alongside ski area.  Charming house in Middlefield, 2 hrs from NY or Boston, holiday rental in Portland
Alongside ski area.  Charming house in Middlefield, 2 hrs from NY or Boston, holiday rental in Portland
Alongside ski area.  Charming house in Middlefield, 2 hrs from NY or Boston, holiday rental in Portland

Alongside ski area. Charming house in Middlefield, 2 hrs from NY or Boston

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming Connecticut Hideaway, holiday rental in Portland
Charming Connecticut Hideaway, holiday rental in Portland
Charming Connecticut Hideaway, holiday rental in Portland

Charming Connecticut Hideaway

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Apt in Middletown-Wesleyan, holiday rental in Portland
Private Apt in Middletown-Wesleyan, holiday rental in Portland
Private Apt in Middletown-Wesleyan, holiday rental in Portland

Private Apt in Middletown-Wesleyan

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Family Stays: Middletown, CT, holiday rental in Portland
Family Stays: Middletown, CT, holiday rental in Portland
Family Stays: Middletown, CT, holiday rental in Portland

Family Stays: Middletown, CT

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Modern 3 Bedroom Lake House- Close To Restaurants and Beach Access, holiday rental in Portland
Modern 3 Bedroom Lake House- Close To Restaurants and Beach Access, holiday rental in Portland
Modern 3 Bedroom Lake House- Close To Restaurants and Beach Access, holiday rental in Portland

Modern 3 Bedroom Lake House- Close To Restaurants and Beach Access

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Luxury Estate, Elegant, Private-2 miles from Wesleyan University-The White Lion, holiday rental in Portland
Luxury Estate, Elegant, Private-2 miles from Wesleyan University-The White Lion, holiday rental in Portland
Luxury Estate, Elegant, Private-2 miles from Wesleyan University-The White Lion, holiday rental in Portland

Luxury Estate, Elegant, Private-2 miles from Wesleyan University-The White Lion

Holiday Rental House
9 bedrooms
10 bathrooms
Sleeps 16
Match: Sleeps
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Newly renovated! 3 bedroom apt in downtown Middletown - across from Wesleyan, holiday rental in Portland
Newly renovated! 3 bedroom apt in downtown Middletown - across from Wesleyan, holiday rental in Portland
Newly renovated! 3 bedroom apt in downtown Middletown - across from Wesleyan, holiday rental in Portland

Newly renovated! 3 bedroom apt in downtown Middletown - across from Wesleyan

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown., holiday rental in Portland
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown., holiday rental in Portland
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown., holiday rental in Portland

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Showing results 1-42 of 42
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