Book Holiday Homes in Raymond

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Raymond

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

Cumberland
Book a stay at this family-friendly vacation home in Cumberland Center. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Capt Lyman Stuart, ...
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries

Portland
Book a stay at this family-friendly vacation home in Portland. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Thompson's Point and ...
The Globe House on Munjoy Hill - Walk to Breweries
Rent a room in the gorgeous Holt House

Rent a room in the gorgeous Holt House

Portland
Stay at this vacation home in Portland. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Thompson's Point and Maine Mall are located ...
Rent a room in the gorgeous Holt House
Save an average of 15% on thousands of hotels when you're signed in
Maine Cottage

Maine Cottage

Lyman
Stay at this vacation home in Alfred. Enjoy free WiFi, a water park, and a picnic area. Popular attractions Swan Pond and Kennebunk Pond are located nearby.
Maine Cottage
Private Lakefront Estate with 180 Degree Views

Private Lakefront Estate with 180 Degree Views

Raymond
Stay at this vacation home in Raymond. Enjoy an in-room coffeemaker, in-room fireplaces, and air conditioning. Popular attractions Sebago Lake and Raymond Cape ...
Private Lakefront Estate with 180 Degree Views
Spacious Country Home Freeport, Only 5 min to LL Bean!

Spacious Country Home Freeport, Only 5 min to LL Bean!

Freeport
Book a stay at this family-friendly vacation home in Freeport. Enjoy free WiFi, a garden, and patios. Popular attractions Desert of Maine and Wilbur's of Maine ...
Spacious Country Home Freeport, Only 5 min to LL Bean!
Ultimate Pine Point Beach Family Compound-4 Units, 8 Bedrooms, Yard

Ultimate Pine Point Beach Family Compound-4 Units, 8 Bedrooms, Yard

Scarborough
The price is NZ$4,802 per night from 8 May to 9 May
NZ$4,802
includes taxes & fees
8 May - 9 May
Stay at this vacation home in Scarborough. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Old Orchard Beach Pier and Old Orchard Beach ...
Ultimate Pine Point Beach Family Compound-4 Units, 8 Bedrooms, Yard
Elegant condo - walk to Portland's best restaurants & Old Port

Elegant condo - walk to Portland's best restaurants & Old Port

Portland
The price is NZ$708 per night from 29 Apr to 30 Apr
NZ$708
includes taxes & fees
29 Apr - 30 Apr
Stay at this vacation home in Portland. Enjoy cable/satellite TV service, an in-room coffeemaker, and air conditioning. Popular attractions Thompson's Point ...
Elegant condo - walk to Portland's best restaurants & Old Port
Prime City Living Townhouse by RedAwning

Prime City Living Townhouse by RedAwning

2 out of 5
75 Carleton St, Portland, ME
Fully refundable
The price is NZ$907 per night from 28 Apr to 29 Apr
NZ$907
includes taxes & fees
28 Apr - 29 Apr
Stay at this vacation home in Portland. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Thompson's Point and Maine Mall are located ...
Prime City Living Townhouse by RedAwning
Don't see what you're looking for?
See all available properties in Raymond
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Raymond Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Raymond vacation homes are the perfect way for you to wing it.

Holiday houses in Raymond let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Raymond in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Raymond adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Raymond with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Raymond vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Raymond Holiday Homes essential information

Accommodation
767 Holiday Homes
Lowest Price
NZ$156
Highest Price
NZ$4,802
Popular accommodation
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!, The Globe House on Munjoy Hill - Walk to Breweries, Rent a room in the gorgeous Holt House, Maine Cottage, Private Lakefront Estate with 180 Degree Views, Spacious Country Home Freeport, Only 5 min to LL Bean!, Ultimate Pine Point Beach Family Compound-4 Units, 8 Bedrooms, Yard, Elegant condo - walk to Portland's best restaurants & Old Port, Prime City Living Townhouse by RedAwning

Top trending hotels in Raymond

6 bedroom waterfront cabin -enjoy beautiful sunsets!

6 bedroom waterfront cabin -enjoy beautiful sunsets!

Frye Island
Stay at this vacation home in Raymond. Enjoy free WiFi, tennis courts, and patios. Popular attractions Sebago Lake and Raymond Cape are located nearby.
6 bedroom waterfront cabin -enjoy beautiful sunsets!
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is NZ$254 per night from 26 May to 27 May
NZ$254
includes taxes & fees
26 May - 27 May
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the bar and the helpful staff in ...
The Westin Portland Harborview
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is NZ$378 per night from 29 Apr to 30 Apr
NZ$378
includes taxes & fees
29 Apr - 30 Apr
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the ...
Portland Harbor Hotel
Save an average of 15% on thousands of hotels when you're signed in
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is NZ$156 per night from 30 Apr to 1 May
NZ$156
includes taxes & fees
30 Apr - 1 May
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Clarion Hotel Portland
Don't see what you're looking for?
See all available properties in Raymond
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.