We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Portland Vacation Rentals

Destination
Revenue impacts this sort order. Learn more

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
48 rentals in Portland.
Lake Cottage Getaway, vacation rental in Portland
Lake Cottage Getaway, vacation rental in Portland
Lake Cottage Getaway, vacation rental in Portland

Lake Cottage Getaway

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Deluxe  Condo In Innercity Portland, Oregon, vacation rental in Portland
Deluxe  Condo In Innercity Portland, Oregon, vacation rental in Portland
Deluxe  Condo In Innercity Portland, Oregon, vacation rental in Portland

Deluxe Condo In Innercity Portland, Oregon

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
The following properties within 20 miles of Portland match all your filters:
Tiny Lakefront Cottage!, vacation rental in Portland
Tiny Lakefront Cottage!, vacation rental in Portland
Tiny Lakefront Cottage!, vacation rental in Portland

Tiny Lakefront Cottage!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Peaceful lake cottage #2, vacation rental in Portland
Peaceful lake cottage #2, vacation rental in Portland
Peaceful lake cottage #2, vacation rental in Portland

Peaceful lake cottage #2

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cozy newly remodeled home close to major amenities  in Connecticut a, vacation rental in Portland
Cozy newly remodeled home close to major amenities  in Connecticut a, vacation rental in Portland
Cozy newly remodeled home close to major amenities  in Connecticut a, vacation rental in Portland

Cozy newly remodeled home close to major amenities in Connecticut a

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Lake Front Cottage #7!, vacation rental in Portland
Lake Front Cottage #7!, vacation rental in Portland
Lake Front Cottage #7!, vacation rental in Portland

Lake Front Cottage #7!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Romantic Lakefront Cottage #5, vacation rental in Portland
Romantic Lakefront Cottage #5, vacation rental in Portland
Romantic Lakefront Cottage #5, vacation rental in Portland

Romantic Lakefront Cottage #5

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Amazing Lakefront Property, vacation rental in Portland
Amazing Lakefront Property, vacation rental in Portland
Amazing Lakefront Property, vacation rental in Portland

Amazing Lakefront Property

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!, vacation rental in Portland
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!, vacation rental in Portland
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!, vacation rental in Portland

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Lake Fun: PingPong, Pool Table, Slide, EV Charger, vacation rental in Portland
Lake Fun: PingPong, Pool Table, Slide, EV Charger, vacation rental in Portland
Lake Fun: PingPong, Pool Table, Slide, EV Charger, vacation rental in Portland

Lake Fun: PingPong, Pool Table, Slide, EV Charger

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Lake Front Home....., vacation rental in Portland
Lake Front Home....., vacation rental in Portland
Lake Front Home....., vacation rental in Portland

Lake Front Home.....

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Fun Lake Front Cottage!, vacation rental in Portland
Fun Lake Front Cottage!, vacation rental in Portland
Fun Lake Front Cottage!, vacation rental in Portland

Fun Lake Front Cottage!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cozy Lakefront Cottage #6, vacation rental in Portland
Cozy Lakefront Cottage #6, vacation rental in Portland
Cozy Lakefront Cottage #6, vacation rental in Portland

Cozy Lakefront Cottage #6

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
lakefront estate, vacation rental in Portland
lakefront estate, vacation rental in Portland
lakefront estate, vacation rental in Portland

lakefront estate

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Beautiful modern Farmhouse studio, vacation rental in Portland
Beautiful modern Farmhouse studio, vacation rental in Portland
Beautiful modern Farmhouse studio, vacation rental in Portland

Beautiful modern Farmhouse studio

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Historic Mansion 1841, vacation rental in Portland
Historic Mansion 1841, vacation rental in Portland
Historic Mansion 1841, vacation rental in Portland

Historic Mansion 1841

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
In-Law Suite in Rocky Hill with Private Entrance, vacation rental in Portland
In-Law Suite in Rocky Hill with Private Entrance, vacation rental in Portland
In-Law Suite in Rocky Hill with Private Entrance, vacation rental in Portland

In-Law Suite in Rocky Hill with Private Entrance

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Renovated Apt - 4min walk from Wesleyan & Main St, vacation rental in Portland
Renovated Apt - 4min walk from Wesleyan & Main St, vacation rental in Portland
Renovated Apt - 4min walk from Wesleyan & Main St, vacation rental in Portland

Renovated Apt - 4min walk from Wesleyan & Main St

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cozy condo in heart of CT, vacation rental in Portland
Cozy condo in heart of CT, vacation rental in Portland
Cozy condo in heart of CT, vacation rental in Portland

Cozy condo in heart of CT

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cozy Getaway w/lots of Natural Light :) 5 mins to adventures, vacation rental in Portland
Cozy Getaway w/lots of Natural Light :) 5 mins to adventures, vacation rental in Portland
Cozy Getaway w/lots of Natural Light :) 5 mins to adventures, vacation rental in Portland

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Betty's Boat House, vacation rental in Portland
Betty's Boat House, vacation rental in Portland
Betty's Boat House, vacation rental in Portland

Betty's Boat House

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Modern Apartment in Prime Location (ID1167X633), vacation rental in Portland
Modern Apartment in Prime Location (ID1167X633), vacation rental in Portland
Modern Apartment in Prime Location (ID1167X633), vacation rental in Portland

Modern Apartment in Prime Location (ID1167X633)

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Modern Apartment in Prime Location (ID7508X96), vacation rental in Portland
Modern Apartment in Prime Location (ID7508X96), vacation rental in Portland
Modern Apartment in Prime Location (ID7508X96), vacation rental in Portland

Modern Apartment in Prime Location (ID7508X96)

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cabin Deck House - Formidable Cabin in Laurel Island, vacation rental in Portland
Cabin Deck House - Formidable Cabin in Laurel Island, vacation rental in Portland
Cabin Deck House - Formidable Cabin in Laurel Island, vacation rental in Portland

Cabin Deck House - Formidable Cabin in Laurel Island

Cabin
4 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Country living at its finest - just 10 min to downtown Middletown, vacation rental in Portland
Country living at its finest - just 10 min to downtown Middletown, vacation rental in Portland
Country living at its finest - just 10 min to downtown Middletown, vacation rental in Portland

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Family Friendly,Lakefront Cottage, 1 dock, private, easy access from I 91., vacation rental in Portland
Family Friendly,Lakefront Cottage, 1 dock, private, easy access from I 91., vacation rental in Portland
Family Friendly,Lakefront Cottage, 1 dock, private, easy access from I 91., vacation rental in Portland

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Two bedroom unit on 3rd floor.  Private entrance., vacation rental in Portland
Two bedroom unit on 3rd floor.  Private entrance., vacation rental in Portland
Two bedroom unit on 3rd floor.  Private entrance., vacation rental in Portland

Two bedroom unit on 3rd floor. Private entrance.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
#24 *Serenity* A Lakefront Cottage Retreat, vacation rental in Portland
#24 *Serenity* A Lakefront Cottage Retreat, vacation rental in Portland
#24 *Serenity* A Lakefront Cottage Retreat, vacation rental in Portland

#24 *Serenity* A Lakefront Cottage Retreat

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
The Braswell, vacation rental in Portland
The Braswell, vacation rental in Portland
The Braswell, vacation rental in Portland

The Braswell

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Little House on River - architectural gem, vacation rental in Portland
Little House on River - architectural gem, vacation rental in Portland
Little House on River - architectural gem, vacation rental in Portland

Little House on River - architectural gem

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cabin Deck House - Formidable Cabin in Laurel Island, vacation rental in Portland
Cabin Deck House - Formidable Cabin in Laurel Island, vacation rental in Portland
Cabin Deck House - Formidable Cabin in Laurel Island, vacation rental in Portland

Cabin Deck House - Formidable Cabin in Laurel Island

Rental Home
4 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cozy, Pet-Friendly Apartment Near University, vacation rental in Portland
Cozy, Pet-Friendly Apartment Near University, vacation rental in Portland
Cozy, Pet-Friendly Apartment Near University, vacation rental in Portland

Cozy, Pet-Friendly Apartment Near University

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Modern Middletown Retreat, 2 Mi to CT River!, vacation rental in Portland
Modern Middletown Retreat, 2 Mi to CT River!, vacation rental in Portland
Modern Middletown Retreat, 2 Mi to CT River!, vacation rental in Portland

Modern Middletown Retreat, 2 Mi to CT River!

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Perfect Hideaway vacation home, vacation rental in Portland
Perfect Hideaway vacation home, vacation rental in Portland
Perfect Hideaway vacation home, vacation rental in Portland

Perfect Hideaway vacation home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Direct Lakefront, 2 docks, private, easy access from I 91., vacation rental in Portland
Direct Lakefront, 2 docks, private, easy access from I 91., vacation rental in Portland
Direct Lakefront, 2 docks, private, easy access from I 91., vacation rental in Portland

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Luxury Waterfront Lake House by Ski Resort & Winery, vacation rental in Portland
Luxury Waterfront Lake House by Ski Resort & Winery, vacation rental in Portland
Luxury Waterfront Lake House by Ski Resort & Winery, vacation rental in Portland

Luxury Waterfront Lake House by Ski Resort & Winery

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Inspiring Lake Views 365 Days a YEAR! What will stay look like?, vacation rental in Portland
Inspiring Lake Views 365 Days a YEAR! What will stay look like?, vacation rental in Portland
Inspiring Lake Views 365 Days a YEAR! What will stay look like?, vacation rental in Portland

Inspiring Lake Views 365 Days a YEAR! What will stay look like?

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Clarke's Landing, vacation rental in Portland
Clarke's Landing, vacation rental in Portland
Clarke's Landing, vacation rental in Portland

Clarke's Landing

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Bell House w/ Lake Access & Massive Deck, vacation rental in Portland
Bell House w/ Lake Access & Massive Deck, vacation rental in Portland
Bell House w/ Lake Access & Massive Deck, vacation rental in Portland

Bell House w/ Lake Access & Massive Deck

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Escape to your lakeside paradise, vacation rental in Portland
Escape to your lakeside paradise, vacation rental in Portland
Escape to your lakeside paradise, vacation rental in Portland

Escape to your lakeside paradise

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Charming private home on the Connecticut River that comfortably sleeps 11 people, vacation rental in Portland
Charming private home on the Connecticut River that comfortably sleeps 11 people, vacation rental in Portland
Charming private home on the Connecticut River that comfortably sleeps 11 people, vacation rental in Portland

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

Rental Home
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Country retreat with pool, brook and waterfall, 2 hours from NYC and Boston, vacation rental in Portland
Country retreat with pool, brook and waterfall, 2 hours from NYC and Boston, vacation rental in Portland
Country retreat with pool, brook and waterfall, 2 hours from NYC and Boston, vacation rental in Portland

Country retreat with pool, brook and waterfall, 2 hours from NYC and Boston

Rental Home
5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
�A Lakefront Sunrise retreat for Couples or Families�, vacation rental in Portland
�A Lakefront Sunrise retreat for Couples or Families�, vacation rental in Portland
�A Lakefront Sunrise retreat for Couples or Families�, vacation rental in Portland

�A Lakefront Sunrise retreat for Couples or Families�

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Magnificent river front home located directly on the CT River, vacation rental in Portland
Magnificent river front home located directly on the CT River, vacation rental in Portland
Magnificent river front home located directly on the CT River, vacation rental in Portland

Magnificent river front home located directly on the CT River

Rental Home
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
The White Lion Manor~Luxury mansion, elegant, secluded. 10 min from Wesleyan, vacation rental in Portland
The White Lion Manor~Luxury mansion, elegant, secluded. 10 min from Wesleyan, vacation rental in Portland
The White Lion Manor~Luxury mansion, elegant, secluded. 10 min from Wesleyan, vacation rental in Portland

The White Lion Manor~Luxury mansion, elegant, secluded. 10 min from Wesleyan

Rental Home
9 bedrooms
10 bathrooms
Sleeps 16
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
CT elegance, stately, private, 2 miles from Wesleyan University-The White Lion, vacation rental in Portland
CT elegance, stately, private, 2 miles from Wesleyan University-The White Lion, vacation rental in Portland
CT elegance, stately, private, 2 miles from Wesleyan University-The White Lion, vacation rental in Portland

CT elegance, stately, private, 2 miles from Wesleyan University-The White Lion

Rental Home
9 bedrooms
10 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
The Little Nest Cottage at Lake Pocotopaug, vacation rental in Portland
The Little Nest Cottage at Lake Pocotopaug, vacation rental in Portland
The Little Nest Cottage at Lake Pocotopaug, vacation rental in Portland

The Little Nest Cottage at Lake Pocotopaug

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Beautiful bungalow style 1br condo, vacation rental in Portland
Beautiful bungalow style 1br condo, vacation rental in Portland
Beautiful bungalow style 1br condo, vacation rental in Portland

Beautiful bungalow style 1br condo

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Showing results 1-48 of 48
Frequently Asked Questions about Portland