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.

Holiday Rentals in Portland

List your property
Owner log in
Where to?
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

1 km
50 rentals in Portland.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order. Learn more.
Deluxe  Condo In Innercity Portland, Oregon, holiday rental in Portland
Deluxe  Condo In Innercity Portland, Oregon, holiday rental in Portland
Deluxe  Condo In Innercity Portland, Oregon, holiday 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
Payment Protection

Inspiring Lake Views 365 Days a YEAR! What will stay look like?, holiday rental in Portland
Inspiring Lake Views 365 Days a YEAR! What will stay look like?, holiday rental in Portland
Inspiring Lake Views 365 Days a YEAR! What will stay look like?, holiday rental in Portland

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out

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
Check-in
Check-out

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
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

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!

Holiday Rental House
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

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
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Spectacular Lakefront home with expansive decks, holiday rental in Portland
Spectacular Lakefront home with expansive decks, holiday rental in Portland
Spectacular Lakefront home with expansive decks, holiday rental in Portland

Spectacular Lakefront home with expansive decks

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

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
More info
Check-in
Check-out

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
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Private Access Studio_king bed_WiFi_all the amenities of a hotel_5⭐️ experience, holiday rental in Portland
Private Access Studio_king bed_WiFi_all the amenities of a hotel_5⭐️ experience, holiday rental in Portland
Private Access Studio_king bed_WiFi_all the amenities of a hotel_5⭐️ experience, holiday rental in Portland

Private Access Studio_king bed_WiFi_all the amenities of a hotel_5⭐️ experience

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Save time - get the best Portland rentals sent straight to your email!
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
More info
Check-in
Check-out

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
More info
Check-in
Check-out

Historic Colonial Farmhouse, holiday rental in Portland
Historic Colonial Farmhouse, holiday rental in Portland
Historic Colonial Farmhouse, holiday rental in Portland

Historic Colonial Farmhouse

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Two bedroom unit on 3rd floor.  Private entrance., holiday rental in Portland
Two bedroom unit on 3rd floor.  Private entrance., holiday rental in Portland
Two bedroom unit on 3rd floor.  Private entrance., holiday 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

Timeless Pre Revolution House with Pool, holiday rental in Portland
Timeless Pre Revolution House with Pool, holiday rental in Portland
Timeless Pre Revolution House with Pool, holiday rental in Portland

Timeless Pre Revolution House with Pool

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out

Resort style heated pool and spa!, holiday rental in Portland
Resort style heated pool and spa!, holiday rental in Portland
Resort style heated pool and spa!, holiday rental in Portland

Resort style heated pool and spa!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Adventure Awaits! Near Attractions, Breakfast, Parking, holiday rental in Portland
Adventure Awaits! Near Attractions, Breakfast, Parking, holiday rental in Portland
Adventure Awaits! Near Attractions, Breakfast, Parking, holiday rental in Portland

Adventure Awaits! Near Attractions, Breakfast, Parking

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

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
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

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
More info
Check-in
Check-out

Betty's Boat House, holiday rental in Portland
Betty's Boat House, holiday rental in Portland
Betty's Boat House, holiday rental in Portland

Betty's Boat House

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Clarke's Landing, holiday rental in Portland
Clarke's Landing, holiday rental in Portland
Clarke's Landing, holiday rental in Portland

Clarke's Landing

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Historic Mansion 1841, holiday rental in Portland
Historic Mansion 1841, holiday rental in Portland
Historic Mansion 1841, holiday rental in Portland

Historic Mansion 1841

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out

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

Cabin Holiday Rental
4 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Nature Escape Getaway! Near Attractions, Parking, Breakfast, holiday rental in Portland
Nature Escape Getaway! Near Attractions, Parking, Breakfast, holiday rental in Portland
Nature Escape Getaway! Near Attractions, Parking, Breakfast, holiday rental in Portland

Nature Escape Getaway! Near Attractions, Parking, Breakfast

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Outdoor Getaway! Near Attractions, Breakfast, Pool, holiday rental in Portland
Outdoor Getaway! Near Attractions, Breakfast, Pool, holiday rental in Portland
Outdoor Getaway! Near Attractions, Breakfast, Pool, holiday rental in Portland

Outdoor Getaway! Near Attractions, Breakfast, Pool

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Outdoor Getaway! Near State Parks & Attractions, Breakfast, holiday rental in Portland
Outdoor Getaway! Near State Parks & Attractions, Breakfast, holiday rental in Portland
Outdoor Getaway! Near State Parks & Attractions, Breakfast, holiday rental in Portland

Outdoor Getaway! Near State Parks & Attractions, Breakfast

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Nature Escape Getaway! Near State Parks & Attractions, Breakfast, holiday rental in Portland
Nature Escape Getaway! Near State Parks & Attractions, Breakfast, holiday rental in Portland
Nature Escape Getaway! Near State Parks & Attractions, Breakfast, holiday rental in Portland

Nature Escape Getaway! Near State Parks & Attractions, Breakfast

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Adventure Awaits! Near State Parks & Attractions, Breakfast, holiday rental in Portland
Adventure Awaits! Near State Parks & Attractions, Breakfast, holiday rental in Portland
Adventure Awaits! Near State Parks & Attractions, Breakfast, holiday rental in Portland

Adventure Awaits! Near State Parks & Attractions, Breakfast

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Outdoor Getaway! 2 Comfortable Units for Business Travel and Adventure, holiday rental in Portland
Outdoor Getaway! 2 Comfortable Units for Business Travel and Adventure, holiday rental in Portland
Outdoor Getaway! 2 Comfortable Units for Business Travel and Adventure, holiday rental in Portland

Outdoor Getaway! 2 Comfortable Units for Business Travel and Adventure

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Nature Escape! 3 Comfortable Units, Pool, Breakfast, Parking, holiday rental in Portland
Nature Escape! 3 Comfortable Units, Pool, Breakfast, Parking, holiday rental in Portland
Nature Escape! 3 Comfortable Units, Pool, Breakfast, Parking, holiday rental in Portland

Nature Escape! 3 Comfortable Units, Pool, Breakfast, Parking

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

Group Vacay! 3 Great Units, Pool, Breakfast, Parking, holiday rental in Portland
Group Vacay! 3 Great Units, Pool, Breakfast, Parking, holiday rental in Portland
Group Vacay! 3 Great Units, Pool, Breakfast, Parking, holiday rental in Portland

Group Vacay! 3 Great Units, Pool, Breakfast, Parking

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

4 Great Units for Large Groups, Near Attractions, Breakfast, holiday rental in Portland
4 Great Units for Large Groups, Near Attractions, Breakfast, holiday rental in Portland
4 Great Units for Large Groups, Near Attractions, Breakfast, holiday rental in Portland

4 Great Units for Large Groups, Near Attractions, Breakfast

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

Adventure Awaits! 4 Convenient Units for Large Groups, Near Attractions, holiday rental in Portland
Adventure Awaits! 4 Convenient Units for Large Groups, Near Attractions, holiday rental in Portland
Adventure Awaits! 4 Convenient Units for Large Groups, Near Attractions, holiday rental in Portland

Adventure Awaits! 4 Convenient Units for Large Groups, Near Attractions

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

Adventure Awaits! 3 Convenient Units, Pool, Breakfast, Parking, holiday rental in Portland
Adventure Awaits! 3 Convenient Units, Pool, Breakfast, Parking, holiday rental in Portland
Adventure Awaits! 3 Convenient Units, Pool, Breakfast, Parking, holiday rental in Portland

Adventure Awaits! 3 Convenient Units, Pool, Breakfast, Parking

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

Adventure Awaits! 2 Great Units for Business Travel and Adventure, holiday rental in Portland
Adventure Awaits! 2 Great Units for Business Travel and Adventure, holiday rental in Portland
Adventure Awaits! 2 Great Units for Business Travel and Adventure, holiday rental in Portland

Adventure Awaits! 2 Great Units for Business Travel and Adventure

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

2 Convenient Units for Business Travel and Adventure, holiday rental in Portland
2 Convenient Units for Business Travel and Adventure, holiday rental in Portland
2 Convenient Units for Business Travel and Adventure, holiday rental in Portland

2 Convenient Units for Business Travel and Adventure

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Nature Escape! 4 Comfortable Units for Large Groups, Near Attractions, Breakfast, holiday rental in Portland
Nature Escape! 4 Comfortable Units for Large Groups, Near Attractions, Breakfast, holiday rental in Portland
Nature Escape! 4 Comfortable Units for Large Groups, Near Attractions, Breakfast, holiday rental in Portland

Nature Escape! 4 Comfortable Units for Large Groups, Near Attractions, Breakfast

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

Beautiful bungalow style 1br condo, holiday rental in Portland
Beautiful bungalow style 1br condo, holiday rental in Portland
Beautiful bungalow style 1br condo, holiday rental in Portland

Beautiful bungalow style 1br condo

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

NEW! Elegant Middlefield Getaway w/ Beach Access!, holiday rental in Portland
NEW! Elegant Middlefield Getaway w/ Beach Access!, holiday rental in Portland
NEW! Elegant Middlefield Getaway w/ Beach Access!, holiday rental in Portland

NEW! Elegant Middlefield Getaway w/ Beach Access!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Amazing updated home in Meriden CT- 5 min from Midstate, holiday rental in Portland
Amazing updated home in Meriden CT- 5 min from Midstate, holiday rental in Portland
Amazing updated home in Meriden CT- 5 min from Midstate, holiday rental in Portland

Amazing updated home in Meriden CT- 5 min from Midstate

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

Guest pavilion in 1814 Historic Home in Middletown, holiday rental in Portland
Guest pavilion in 1814 Historic Home in Middletown, holiday rental in Portland
Guest pavilion in 1814 Historic Home in Middletown, holiday rental in Portland

Guest pavilion in 1814 Historic Home in Middletown

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out

1814 Historic Home in Middletown, holiday rental in Portland
1814 Historic Home in Middletown, holiday rental in Portland
1814 Historic Home in Middletown, holiday rental in Portland

1814 Historic Home in Middletown

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Farm Cottage with incredible hills and orchard views from front and back, holiday rental in Portland
Farm Cottage with incredible hills and orchard views from front and back, holiday rental in Portland
Farm Cottage with incredible hills and orchard views from front and back, holiday rental in Portland

Farm Cottage with incredible hills and orchard views from front and back

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Renovated Apt - 4min walk from Wesleyan & Main St, holiday rental in Portland
Renovated Apt - 4min walk from Wesleyan & Main St, holiday rental in Portland
Renovated Apt - 4min walk from Wesleyan & Main St, holiday rental in Portland

Renovated Apt - 4min walk from Wesleyan & Main St

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out

Entire place for yourself  Middletown/Cromwell line, holiday rental in Portland
Entire place for yourself  Middletown/Cromwell line, holiday rental in Portland
Entire place for yourself  Middletown/Cromwell line, holiday rental in Portland

Entire place for yourself Middletown/Cromwell line

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out

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
More info
Check-in
Check-out

Country retreat with pool, brook and waterfall, 2 hours from NYC and Boston, holiday rental in Portland
Country retreat with pool, brook and waterfall, 2 hours from NYC and Boston, holiday rental in Portland
Country retreat with pool, brook and waterfall, 2 hours from NYC and Boston, holiday rental in Portland

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

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out

Lake Fun: PingPong, Pool Table, Slide, EV Charger, holiday rental in Portland
Lake Fun: PingPong, Pool Table, Slide, EV Charger, holiday rental in Portland
Lake Fun: PingPong, Pool Table, Slide, EV Charger, holiday rental in Portland

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out

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
More info
Check-in
Check-out

Magnificent custom built French Chateau /Bungalow / Private Resort, holiday rental in Portland
Magnificent custom built French Chateau /Bungalow / Private Resort, holiday rental in Portland
Magnificent custom built French Chateau /Bungalow / Private Resort, holiday rental in Portland

Magnificent custom built French Chateau /Bungalow / Private Resort

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

PreviousNext
1
Frequently Asked Questions about Portland