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
With a stay at this vacation home, you'll be centrally located in Cumberland Center, within a 15-minute drive of Thompson's Point and LL Bean Flagship ...
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
With a stay at this vacation home, you'll be centrally located in Portland, within a 10-minute drive of Thompson's Point and Maine Mall.
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
With a stay at this vacation home in Portland (Parkside), you'll be a 3-minute drive from Thompson's Point and 8 minutes from Maine Mall.
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
Located in Alfred, this vacation home is on a lake, within a 15-minute drive of Swan Pond and Kennebunk Pond.
Maine Cottage
Private Lakefront Estate with 180 Degree Views

Private Lakefront Estate with 180 Degree Views

Raymond
With a stay at this vacation home in Raymond, you'll be steps from Sebago Lake and Jordan Bay.
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
With a stay at this vacation home in Freeport, you'll be by the sea, within a 10-minute drive of LL Bean Flagship Store and Casco Bay.
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 AU$4,519 per night from 8 May to 9 May
AU$4,519
includes taxes & fees
8 May - 9 May
With a stay at this vacation home in Scarborough (Grand Beach), you'll be within a 5-minute drive of Old Orchard Beach and Old Orchard Beach Pier.
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 AU$664 per night from 13 May to 14 May
AU$664
includes taxes & fees
13 May - 14 May
With a stay at this vacation home, you'll be centrally located in Portland, a 5-minute drive from Thompson's Point and 9 minutes from Maine Mall.
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 AU$999 per night from 14 May to 15 May
AU$999
includes taxes & fees
14 May - 15 May
With a stay at this vacation home in Portland (Parkside), you'll be a 4-minute drive from Thompson's Point and 8 minutes from Maine Mall.
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
AU$160
Highest Price
AU$4,519
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
With a stay at this vacation home in Raymond, you'll be on the waterfront, just steps from Sebago Lake.
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 AU$266 per night from 27 May to 28 May
AU$266
includes taxes & fees
27 May - 28 May
With a stay at The Westin Portland Harborview, you'll be centrally located in Portland, steps from State Theatre and Portland Museum of Art.
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 AU$352 per night from 4 May to 5 May
AU$352
includes taxes & fees
4 May - 5 May
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, a 5-minute drive from Thompson's Point and 9 minutes from Maine Mall.
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 AU$160 per night from 4 May to 5 May
AU$160
includes taxes & fees
4 May - 5 May
With a stay at Clarion Hotel Portland in Portland, you'll be near the airport, within a 15-minute walk of Thompson's Point and Portland Exposition Building.
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.